Abstract
Macrocyclic compounds play an important role in supramolecular chemistry accounting for their unique recognition and self-assembly properties and potential applications in biomedicine and material science. Azo compounds display promising capability in fields of molecular switches, polymers, smart materials and molecular machines because of their photoactive and electroactive properties. Introducing azo groups into macrocycles gives them signal moieties, additional recognition sites, photo-responsive properties, and so on. Herein, we comprehensively review the structures of azo-containing macrocyclic compounds reported up to now. Then we describe representative works on azo macrocycles with their molecular recognition, self-assembly and application emphasized.
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Introduction
Macrocyclic chemistry has become a major topic of supramolecular chemistry because of the unique recognition properties [1], serving as self-assembly building blocks [2,3,4] and potential applications in biomedicine [5,6,7], and material science [8,9,10,11]. A lot of macrocycles, typically crown ethers, cyclodextrins, calixarenes, and cucurbiturils, have been developed and investigated extensively [12]. In recent years, stimuli-responsive molecular recognition and self-assembly have gained more and more attention, and demonstrated abundant applications in various fields. Conventional stimulating modalities include temperature, pH, light, electric, enzyme, and so on. Among these stimuli, light is especially appealing for its cleanness, non-invasion and high spatiotemporal resolution [13, 14]. The most commonly used photo-responsive molecules include azobenzene, stilbene, and spiropyran and diarylethene derivatives.
Azo compounds represent more than half of the world production of industrial dyes [15] and most of them displayed reversibly light-driven trans- to cis-isomerization. Cis-isomer is substantially different from trans-isomer in many aspects: larger dipole moment, weaker π–π* and stronger n–π* absorption, more bent geometry and typically less thermodynamically stable. Therefore, they have been widely used to drive photo-responsive molecular switches [16, 17], polymers [18], metal–organic materials [19], liquid crystals [20], and molecular machines [21].
Decorating azo groups on macrocycles is a convenient and powerful way to endow macrocycles with additional physical and chemical properties, such as larger cavity for efficient recognition, guest induced color change for optical sensing, and more importantly, photo-responsive switch of binding affinity, self-assembly behavior and function [22]. Several excellent reviews have summarized the progress in this field [23, 24], but no review summarized the azo-containing macrocycles comprehensively and highlighted their recognition, assembly and application. In this review, we will summarize the structures of azo-containing macrocyclic compounds reported up to now and focus our special attention on their recognition, self-assembly and application. The structure of this review will be such that we first summarize and comprehensively list the structures of different classes of azo macrocycles, including azo crown ether, azo cyclodextrin, azo calixarene, azo resorcinarene, azo calixpyrrole, azo benzenophane, azo porphyrin and others. Then we describe selectively a series of representative works on azo macrocycles with their molecular recognition, self-assembly and application.
Structures of azo macrocycles
Azo crown ethers
Crown ethers, cyclic chemical compounds containing a ring with several ether groups, are the first generation of macrocyclic compounds. In 1967, Pedersen discovered crown ethers and found their binding with alkali metal cation [25]. Crown ethers are represented as [m]crown-n, where m is the total number of atoms and n is the number of oxygen atoms. Crown ethers have been applied in phase transfer catalysis, the decontamination of nuclear waste, and so on [12] (Schemes 1, 2, 3, 4, 5, 6, 7, 8, 9; Tables 1, 2, 3, 4, 5, 6, 7, 8, 9).
Structures of crown ethers with one azo group in a simple ring
Structures of crown ethers with two azo groups in a simple ring
Structures of bis(crown ethers) with one azo group in a simple ring
Structures of bis(crown ethers) with azo groups in complex ring
Structures of bis(crown ethers) linked by azo group
Structures of crown ethers with one azo group on its periphery
Structures of azo crown ethers linked with polymers
Structures of crown ethers with two azo groups on its periphery
Structures of crown ethers with azo groups in complex ring
Azo cyclodextrins
Cyclodextrins, the second generation of macrocyclic compounds, are cyclic oligosaccharides consisting of d-glucose units linked by α-(1,4)-glucose bonds. The most common cyclodextrins consist 6, 7, and 8 glucose units, and are called α-, β-, and γ-cyclodextrins, respectively. They are cylinder shaped and possess hydrophobic inner cavity and hydrophilic outer surface, resulting in their unique complex ability with a variety of lipophilic molecules [164] (Schemes 10, 11; Tables 10, 11).
Structures of azo cyclodextrins with one host unit
Structures of azo cyclodextrins with more than one host unit
Azo calixarenes
Calixarenes are the third generation of macrocyclic compounds composed of phenolic units bridged with methylene groups at o-positions of phenolic hydroxyl groups. Calixarenes with n phenolic units are represented as calix[n]arene and the most studied calixarenes have n = 4, 5, 6, and 8. Calixarenes are facilely modified to introduce various kinds of functional groups and to adjust cavity sizes, which have been described as having “(almost) unlimited possibilities” [213]. Properly modified calixarenes can bind with both metal ions like crown ethers, and hydrophobic molecules like cyclodextrins. A unique property of calixarene is its various conformation. The smallest calix[4]arene have four typical conformations: cone, partial cone, 1,2-alterative, 1,3-alterative [214], while other larger calixarenes have more complex conformational space (Schemes 12, 13, 14, 15, 16, 17, 18; Tables 12, 13, 14, 15, 16, 17, 18).
Structures of azo calixarenes (part 1)
Structures of azo calixarenes (part 2)
Structures of azo calixarenes (part 3)
Structures of azo calixarenes (part 4)
Structures of azo calixarenes (part 5)
Structures of azo calixarenes (part 6)
Structures of azo calixarenes (part 7)
Azo resorcinarenes
Resorcinarenes are a class of macrocycles which are structurally similar to calixarenes. In contrast to calixarenes, the repeat unit of resorcinarenes is resorcinol instead of phenol. Resorcinarenes with n repeat units are represented as resorcin[n]arenes and the most studied resorcinarenes are the resorcin[4]arene [399]. In general, resorcinarenes can be synthesized by acid-catalyzed condensation of resorcinol or its derivatives with aldehyde [400]. Various methods were developed for their functionalization to synthesize sophisticated derivatives [399] (Schemes 19; Table 19).
Structures of azo resorcinarenes
Azo calixpyrroles
Calixpyrroles are a class of hetero-calixarenes containing pyrrole units linked by meso-carbon bridges. Calixpyrroles can be obtained by the condensation of pyrrole and ketones. Sessler and co-workers first found they can bind anion guests [424] and be used to construct ion-pair receptors [425]. They have been utilized for sensing [426], extracting [427] and transporting [428] of anions (Scheme 20, Table 20).
Structures of azo calixpyrroles
Azobenzenophanes
Azobenzenophanes are cyclic oligomer of azobenzenes with unique isomerization properties [22]. They have potential applications in constructing multistate switches and overcoming the instability of Z-isomer of azobenzene (Scheme 21, Table 21).
Structures of azobenzenophanes
Azo porphyrins
Porphyrins are a class of planar macrocycle with four pyrrolic subunits bridged by methine units. Porphyrins are involved in various biological processes, such as oxygen binding, photosynthesis and electron transfer. They are also used as photosensitizer in photodynamic therapy and artificial light harvesting system (Scheme 22, Table 22).
Structures of azo porphyrins
Others
Although the above compounds covered most of azo macrocycles, some azo containing macrocyclic molecules not belong to derivatives of typical macrocycles. Here, we classified these compounds as others (Schemes 23, 24, 25, 26, 27; Tables 23, 24, 25, 26, 27).
Structures of other azo macrocycles (part 1)
Structures of other azo macrocycles (part 2)
Structures of other azo macrocycles (part 3)
Structures of other azo macrocycles (part 4)
Structures of other azo macrocycles (part 5)
Recognition, self-assembly and application
In this section, we describe selectively the following 30 representative works on azo-containing macrocycles to demonstrate their recognition, self-assembly and application.
Recognition
Early in 1979, Ueno et al. reported an azobenzene-capped β-cyclodextrin (β-CD) that can regulate the 1:2 host–guest complexation and its binding ability by cis/trans photoisomerization of azobenzene in response to light stimulus (Fig. 1) [191]. Reaction of β-CD with 4,4′-bis(chlorocarbonyl)-trans-azobenzene afforded compound 349 (see Scheme 10) in 20% yield. Upon irradiation, 349 was converted into its cis-isomer with a much larger cavity. For most of tested aromatic and olefinic guests, the cavity of cis-isomer is large enough to encapsulate two guests. All tested guests show higher binding affinities with the cis-isomer than with the trans-isomer. The most striking feature took place in binding 4,4′-bipyridine. 349 cannot bind 4,4′-bipyridine when the azobenzene group is in its trans form. However, upon irradiation with UV light, it converts to cis-isomer, and then the host includes 4,4′-bipyridine in its expanded cavity, as indicated by circular dichroism experiments. When cis 349 reverses to its trans-isomer in the dark, 4,4′-bipyridine is ejected from the cavity.
Reproduced with permission from Ref. [191]. Copyright 1979 from American Chemical Society
Illustration of isomerization and complexation with guest of 349.
In 1992, the same group synthesized a color change indicator in acidic solution 325 (see Scheme 10) by appending one methyl red dye to 6-deoxy-6-amino-β-CD (Fig. 2) [165]. Methyl red shows color change depending on the pH conditions. The dye moiety is included in the hydrophobic cavity of β-CD, which protects it from protonation. Therefore, the dye-appended β-CD remains yellow in acidic solution. The color change will occur when an organic guest displaces the methyl red dye from the interior of β-CD, which makes the dye moiety available to protonation. It should be possible to exploit the molecular recognition capability of β-CD to develop a range of such indicators.
Reproduced with permission from Ref. [165]. Copyright 1992 from Nature Publishing Group
Illustration of the guest-induced conformational change of 325 that causes the color change.
In 2017, Hayashita and co-workers reported an azobenzene bearing γ-CD derivative 350 (see Scheme 10) for recognizing phosphoric acid derivatives (Fig. 3) [194]. Compound 350 shows high selectivity towards adenosine triphosphate (ATP) over other tested phosphoric acid derivatives: monophosphate, pyrophosphate, triphosphate, adenosine monophosphate and adenosine diphosphate. Moreover, the absorption spectrum of 350 responds to ATP specifically even if other analogues existed. The Cu2+ complex of compound 350 forms 1:1 complex towards ATP with binding constant 6640 M−1, accompanied with remarkable blue shift in the absorption spectrum. 1H NMR experiments revealed that adenine moiety of ATP existed in the γ-CD cavity. Dipicolylamine moiety provides additional recognition site for phosphoric groups of ATP. The cooperation of these interactions probably results in the high selectivity to ATP.
Reproduced with permission from Ref. [194]. Copyright 2017 from American Chemical Society
a Selective sensing to ATP by Cu·350 in the presence of phosphoric acid derivatives. b Suggested structure of Cu·350/ATP complex.
In 2006, Chun et al. reported a nitroazophenolic crown ether 219 (see Scheme 6) with asymmetric centers for enantiomeric recognition of amines [135]. Spectrophotometric method verified that the binding of amines resulted in changes of the absorption spectrum of the host, and that two enantiomers formed complexes with different stabilities. The recognition process can also be monitored by cyclic voltammetry. The oxidation of the phenol group of 219 shows a single peak at voltammograms. The addition of an alkyl amine is accompanied by a new oxidation wave at potentials that are different for each enantiomer. The difference between the oxidation potentials of the complexes formed by 219 with two enantiomers of 2-amino-2-phenylethanol is 44 mV. This method allows quantifying the ratio of enantiomers in an R/S mixture because the peak potential of 219 varied linearly with the enantiomer ratio.
In 1998, Kim and Chang reported a calix[4]arene chromophore 928 (see Scheme 18) with two distal azophenol moieties [391]. NMR data showed 928 adopted a syn-oriented conformation. Binding of Ca2+ by 928 was determined by extraction between CaCl2 solution at pH 7 and CHCl3 contain host 928. A bathochromic shift from 437 to 605 nm was observed (Fig. 4) and the solution color changed from yellow to greenish blue. Other similar cations induced no shift at comparable concentrations and the selectivity to Ca2+ over them were 195 (Sr2+), 725 (Mg2+) and 680 (Na+). The nitrogen atoms on 928 are important for both binding at neutral condition and Ca2+ selectivity.
Reproduced with permission from [391]. Copyright 1998 from American Chemical Society
UV absorption spectra of 928 upon extraction with aqueous metal chloride solution.
In 2012, Pulpoka and co-workers described a selective fluoride sensor based on an azo calix[4]arene-strapped calix[4]pyrrole 473 (see Scheme 17) [269]. The color modulation of CH3CN solution of 473 was observed in the presence of certain anions, which was also reflected in distinctive absorption changes. Upon addition of six equivalents of F−, a bathochromic shift from 395 nm to about 600 nm in the absorption spectrum of 473 was observed. Other tested anions only imparted much smaller, if not negligible, absorption changes. The spectroscopic changes upon basic anions complexation were ascribed to the modulation of charge transfer from the oxygen of azophenol moieties to the nitrophenyl chromophores. Spectroscopic analyses showed the formation of both 1:1 and 1:2 complexes for F−. By adding Ca(NO3)2 into a solution of the 473·F− complex, the F− ions were salted out in the form of CaF2, which resulted in the recovery of the original orange color of free receptor 473 (Fig. 5). In contrast, when Ca(NO3)2 was added to the corresponding CH3COO−, BzO−, or H2PO4− complexes, ion-pair complexes were formed without noticeable color changes.
Reproduced with permission from Ref. [269]. Copyright 2011 from American Chemical Society
F− coordination by 473 and displacement by Ca(NO3)2.
In 1985, Kaneda et al. developed a series of novel spherand azophenol dyes 1236 (see Scheme 26), displaying Li+-specific colouration [560]. The crystal structure of 1236a (Fig. 6), an analogue of 1236, showed that the radius of the cavity is 0.68 Å. This radius is compatible with the ionic radius of Li+ (0.60 or 0.73 Å) and is smaller than that of Na+ (0.95 or 1.16 Å). In chloroform, only lithium salt in 63 kinds of salts leads to the change in absorption spectrum in the presence of excess piperidine as base, with a remarkable color change from yellow to violet. The “perfect” selectivity is obtained due to the steric effect caused by the narrow entrance to the cavity rejects larger cations.
Reproduced with permission from Ref. [560]. Copyright 1985 from American Chemical Society
Molecular structure of 1236a shown by the ORTEP drawing.
In 1988, the same group studied the binding properties of azophenol crown ether 255 (see Scheme 6) containing a benzoic acid moiety [116]. The solution of 255 was yellow and showed absorption maxima at 400 nm in chloroform. Large red shift of its UV–Vis spectrum could be observed when 255 formed complexes with amines. The solution color turned to blue with monoamines while to pink with diamines, indicating a very different coloration based on the two ionic binding sites in the crown cavity. Titration experiments show that 255 forms a 1:1 complexes with some equivalents of diamines and 1:2 complexes with large excess of diamines. The molecular structure of the salt complex between 255 and piperazine was determined by X-ray crystal analysis (Fig. 7). In the 255·piperazine complex, the protonated piperazine is sandwiched between phenolate and benzoate planes in “chair” form. Strong hydrogen bonds are formed between the phenolic oxygen atoms of 255 and the piperazine guest.
Reproduced with permission from Ref. [116]. Copyright 1988 from American Chemical Society
An ORTEP drawing of the molecular structure of the 255·piperazine complex.
In 2011, Rebek and co-workers synthesized photoswitchable cavitands 977 and 978 (see Scheme 19) bearing the azo moiety as one of the walls [415]. The thermal- and photo-isomerization behaviors of azo cavitands 977 and 978 were analyzed in d12-mesitylene (Fig. 8). Trans–cis photo-isomerization is achieved by illuminating with 365 nm light for 15 min to reach a photostationary state. Cis–trans conversion can be achieved by heating to 164 °C for 5 min or irradiating with light longer than 450 nm for 20 min. Trans–cis and cis–trans cycles can be repeated 5 times without degradation of the system. Both the trans-isomers of 977 and 978 are able to bind neutral adamantane guests. The binding behaviors of trans azo cavitands 977 and 978 were studied in d12-mesitylene. The highest values of stability constants were observed for 1-adamantanecarbonitrile and 2-adamantanone, which can interact with the amide on the upper rim of cavitands. The complexation of adamantane guests can be light-controlled for 978, but not for 977 without tert-butyl substitution. This striking contrast is because the bound guest is replaced with an introverted tert-butyl.
Reproduced with permission from Ref. [415]. Copyright 2011 from Royal Society of Chemistry. (Color figure online)
1H NMR spectra in d12-mesitylene showing trans-978 (bottom) and self-contained cis-978 (top). The inverted tert-butyl signal is marked by a blue circle.
In 2016, Scherman and co-workers described the synthesis and photo-responsive binding properties of macrocycle 1220 containing bis(imidazolium)-azobenzene motifs (Fig. 9) [553]. NMR analysis revealed macrocycle 1220 existed as all-trans stereoisomer in a freshly prepared trideuterioacetonitrile solution. Isomerization products generated by irradiating UV light were a mixture of stereoisomers E,E-1220 (18%), E,Z-1220 (38%) and Z,Z-1220 (44%). Visible light illumination causes the photostationary state E,E-1220 as the main isomer. Stereoisomer E,E-1220 could complex with 4,4′-dipyridyl-N,N′-dioxide (4DPDO), 4-phenylpyridine N-oxide and biphenyl-4,4′-dicarboxylate. Irradiation of the complex with UV light induced the trans- to cis-isomerization of the azo groups, resulting in the 4DPDO guest release from the cavity. Further exposure of the mixture to visible light reverts the guest encapsulation into the macrocycle cavity.
Reproduced with permission from Ref. [553]. Copyright 2016 from Wiley-VCH Verlag GmbH & Co. KGaA
Schematic representation of the photo-controlled catch and release of 4DPDO by 1220.
Self-assembly
In 2008, Liu et al. used click chemistry to covalently connect the host and guest in threaded β-CD-based azobenzene complexes (Fig. 10) [172]. Azobenzene substituted with propargyl alcohol was coupled to azide functionalized β-CD, forming different isomers depending on the reaction conditions. The hydrothermal 1,3-cycloaddition led to self-locked isomer 334a (see Scheme 10), whereas Cu(I) catalyzed click chemistry gave the self-unlocked isomer 334b. A possible mechanism for the synthesis of 334a involved the primary formation of the inclusion complex of β-CD with azobenzene, and the subsequent reaction between the azido group of β-CD with the ethynyl group of azobenzene. In aqueous solution and in solid state, 334a formed dimer capsule, in which the azobenzene moieties were included by both its own cavity and the cavity of the second β-CD, as demonstrated by ROESY-NMR and solid state structure. In DMSO, however, 1H NMR spectroscopy shows that 334a existed as the monomeric self-locked conformer, which could be regarded as a new type of [1] rotaxane without a stopper. In water–DMSO mixture, 334b assembled to linear oligomeric supramolecule, as demonstrated by high resolution TEM and FTICR-MS. The above study shows that the spatial arrangement factor can be of great importance for the self-assembling morphology.
Reproduced with permission from Ref. [172]. Copyright 2008 from American Chemical Society
Deduced self-assembly structures of 334a (top) and 334b (bottom).
In 2015, the same group reported the photo-controlled nanotube–nanoparticle conversion for the assembly of an amphiphilic porphyrin derivative and azobenzene-bridged bis(permethyl-β-CDs) 365 (see Scheme 11 and Fig. 11) [207]. The porphyrin derivative could form aggregates with an average hydrodynamic diameter about 180 nm. Upon addition of trans-365 in solution of the porphyrin derivative, the morphology of the aggregate transformed to secondary assembly nanotubes, which is revealed by TEM images. The average inner and outer diameters of the nanotubes were about 45 and 61 nm with a wall thickness of about 8 nm. Upon photoisomerization the nanotubes reversibly changed to nanospheres with the average diameter of 180–220 nm.
Reproduced with permission from Ref. [207]. Copyright 2015 from Wiley-VCH Verlag GmbH & Co. KGaA
Illustration of the secondary assembly of amphiphilic porphyrin derivative mediated by trans-365.
In 2013, Aseyev and co-workers synthesized polymer 443 (see Scheme 15) with azo calix[4]arene in the main chain that was substituted with tetraethylene glycol monomethyl ether chains [254]. The poly(azo calix[4]arenes) exhibited lower critical solution temperature behavior in aqueous solution and upper critical solution temperature behavior in alcohols. In alcohols, the phase transition temperature of the polymers decreases proportionally with increasing the cis content by irradiating with 365 nm light. The cloud point can be modulated by irradiation or thermal relaxation depending on the trans/cis ratio of the azobenzene groups. The 365 nm light assisted writing on solutions of the polymer in alcohols can be realized (Fig. 12).
Reproduced with permission from Ref. [254]. Copyright 2013 from American Chemical Society
Photographs of poly(azo calix[4]arenes) 443 in ethanol: a at 20 °C before irradiation; b after photoassisted writing at 20 °C; c at 40 °C and d at 20 °C after thermal relaxation.
In 2016, Ballester and co-workers developed a heterodimeric capsule containing an azobenzene-appended calix[4]arene 638 (see Scheme 18) and a tetraurea calix[4]pyrrole without azobenzene 638a in the presence of polar guests [289]. In the presence of trimethylphosphine oxide guest, irradiating the heterodimeric capsule results in the formation of all-cis-638·638a capsule, indicating photo-isomerization in only half of capsule is not sufficient to cause the disassembly of the capsule. In a more complicated system, in which both trimethylphosphine oxide and bis-(N-oxide N,N,N′,N′-tetramethylamino)hexane existed, two capsules, 638·638a and 638a·638a, are formed at the same time and the equilibrium between them can be modulated by light.
In 2014, the same group further developed a tetraurea aryl extended calix[4]pyrrole 1007 (see Scheme 20) with four azobenzene groups at the upper rim [437]. By encapsulating 4,4′-bipyridine bis-N,N′-oxide as a template, 1007 assembles into a hydrogen-bonded dimeric capsule (Fig. 13). The capsule can be detected by 1H NMR spectroscopy in solution only when all azobenzene units are in trans forms. The capsule disintegrates when irradiated with 400 nm light and reassembles after cis-to-trans relaxation in the dark. They further presented photo-responsive homodimeric and heterodimeric capsules using two novel calix[4]pyrrole [433]. This study may be further developed to photo-responsive drug delivery if can operate in aqueous media.
Reproduced with permission from [437]. Copyright 2014 from Royal Society of Chemistry
Structures of arylextended tetraurea calix[4]pyrrole and bis-pyridine-N-oxide (left) and energy minimized structure of the capsular assembly (right).
In 2008, Gin and co-workers prepared a shape-switchable metallacycle 1259 (see Scheme 27) bearing azobenzene units via coordination-driven self-assembly [572]. The Pt containing metallacycle forms mesogen at room temperature in a thermotropic columnar liquid crystal (LC) phase, which was swollen in polar solvents (dioxane, diglyme, and ethylene glycol) to further form a lyotropic LC phase (Fig. 14). For the lyotropic LC state of unpolymerised 1259, irradiation with 375 nm light resulted in conversion to the cis-isomer, accomplished by phase transition from a liquid crystalline phase to an isotropic phase. However, cross-linking the lyotropic LC assembly led to a nanostructured polymer network, preventing disruption of the LC order when photoconversion to the cis-isomers upon UV irradiation. The material may be useful to drug-delivery or controlled nanofiltration applications.
Reproduced with permission from Ref. [572]. Copyright 2008 from Wiley-VCH Verlag GmbH & Co. KGaA
Proposed, idealized model of the thermotropic columnar hexagonal LC phase of 1259 (left). Addition of polar solvent serves to swell this phase (right).
In 2011, Norikane et al. developed photo-responsive liquid crystallines based on azobenzenophanes 1021 and 1022 (see Scheme 21 and Fig. 15) [481]. The self-assembling material can be switched by light. In the liquid crystalline state, dimer 1021 behaves as a rod-like molecule exhibiting smectic phases, while the disk-like trimer 1022 forms columnar phases. These materials exhibit isothermal phase transition from liquid crystalline to isotropic state upon UV light irradiation because of shape change of the molecules. The liquid crystalline phase forms again upon heating the isotropic phase at 120 °C for 10 s. Such photo-responsive materials could be useful in applications to photolithography and photo-responsive adhesives.
Reproduced with permission from Ref. [481]. Copyright 2011 from Royal Society of Chemistry
Polarizing optical photomicrographs of 1021 at 120 °C (a–c) and 1022 at 25 °C (d–f) before 365 nm light UV irradiation (a, d), during irradiation for 5 s (b, e) and 10 s after ceasing the irradiation (c, f). The initial states are SmC (a) and columnar (d) phases. The dark area in (b–f) corresponds to an isotropic phase.
In 2009, Wang and co-workers integrated four azobenzene units in the backbone of azobenzenophane 1015 (see Scheme 21) by connecting through intermediate carbazole groups [474]. Although 1015 does not form an extended 2D network on its own, self-assembled monolayers of host–guest networks were observed by mixing it with 1,3,5-tris(10-carboxydecyloxy)-benzene (TCDB) on a highly ordered pyrolytic graphite surface. Depending on the mixing ratio of TCDB and the macrocycle, the TCDB network captures either a monomer or a dimer of 1015. The structures of the networks dependent on the isomers of 1015 can be distinguished by scanning tunneling microscopy, which revealed that all the azo groups are in the trans form (t,t,t,t). Upon irradiation of the monolayer by 366 nm light, azobenzene units of the macrocycle partially isomerize and give rise to different isomers including trans–trans–trans–cis (t,t,t,c) and trans–cis–trans–cis (t,c,t,c) isomers (Fig. 16).
Reproduced with permission from Ref. [474]. Copyright 2009 from American Chemical Society
Molecular models of the conformational and photoisomers of 1015 in the photoisomerization.
In 2013, Wegner and Reuter reported an azobenzene macrocycle 1223 (see Scheme 25) displaying the light-controlled switchable π-stacking (Fig. 17) [482]. 1223 can form 3D networks through significant π-stacking interactions. Light-controlled sol–gel transition of 1223 could be observed only in aromatic solvents, because they are incorporated inside the 3D π-stacking network. These results suggested that 1223 might be useful for building up materials for small molecules controlled release by light stimulation.
Reproduced with permission from Ref. [482]. Copyright 2013 from Royal Society of Chemistry
Schematic representation of 3D-networks dimeric switchable azobenzene macrocycle 1223. In the all-E conformation linked p-stacks are formed (left). Irradiation induces isomerization to a mixture of Z-isomers all deviating from planarity, which impedes the supramolecular interaction (right).
In 2017, Xie et al. synthesized a carbohydrate-based macrocyclic azobenzene 1272 (see Scheme 27) using one-pot O-alkylation mediated macrocyclization approach [574]. 1272 exhibits reversible photo-isomerization between trans-and cis-isomers upon irradiation of light with different wavelengths. Moreover, thermal stability of the cis-isomer (t1/2 = 51 days) is better than of the acyclic analogue (t1/2 = 19 days). Circular dichroism study revealed the chirality transfer from the sugar unit to azobenzene, which adopts preferentially P-helicity for both trans-and cis-isomers. In cyclohexane and ethanol, 1272 can form organogels, which are responsive to temperature, light and mechanical force (Fig. 18). Furthermore, 1272 displays a helical transition behavior during gelation that can be modulated by changing temperature.
Reproduced with permission from Ref. [574]. Copyright 2017 from Wiley-VCH Verlag GmbH & Co. KGaA
Pictures showing the multi stimuli-responsive behavior of gel of 1272 in cyclohexane.
Application
Based on the exploration of recognition, self-assembly and other properties, the chemistry of azo macrocycles gives rise to several applications. Here, we highlight a few of them containing selective sensing and imaging, photocontrolled supramolecular catalysis, molecular machine, and so on.
Azo isomerization mechanism
In 1982, Rau and Lueddecke synthesized two azobenzenophanes 1049 and 1069 (see Scheme 21) for application in studying trans–cis-isomerization mechanism of azobenzenes [484]. For the photoisomerization, two different pathways have been proposed: a rotation around the N–N double bond and a direct inversion of the orientation of one of the phenyl rings. For the two macrocycles, inversion was the only possible isomerization pathway because of the steric hindrance. The quantum yield of the trans–cis-isomerization was 0.24 for n–π* excitation of 1049, which is similar to that of azobenzene (0.23). This indicates that the trans–cis-isomerization of azobenzene under n–π* excitation is through an inversion mechanism.
Sensing and imaging
Although some works involved in sensing have been described in the section of recognition, we herein discuss sensing for works closer to practical application. In 1992, Kumar and co-workes reported a small-cavity cryptand phenol 319 (see Scheme 9) which could be applied for the colorimetric determination of lithium in blood serum without sample pretreatment or solvent extraction [161]. The compound 319 exhibits a greater than 4000:1 selectivity for lithium over sodium due to rigid configuration of a well-preorganized binding site for lithim complexation. The standard curve for lithium is linear up to 3.5 mM and contains the therapeutic range. Serum was diluted 40 times for the measurement and the obtained results for serum spiked with lithium correlated well with flame photometry measurements.
In 2010, Lang and co-workers developed a pH sensor 549 (see Scheme 18) based on azo calix[4]arene bearing four carboxyl groups [319]. The crystal structure obtained in DMF solution revealed that 549 adopt a flattened cone conformation. Moreover, the aqueous solution of 549 displayed distinct color change responding to pH in the range of 1–13, which is broad than most of pH sensing compounds (Fig. 19). The color change is reversible, suggested that 549 may have a potential application as a good pH sensor.
Reproduced with permission from Ref. [319]. Copyright 2010 from Wiley-VCH Verlag GmbH & Co. KGaA. (Color figure online)
a UV–Vis spectra of 549 titrated with a dilute NaOH solution. b Color changes corresponding to different pH values.
Peoples are interested in concentrations of biological molecules, not only in tissue and body fluid but also in single cell level, in which fluorescence imaging is highly on demand. In 2016, Yilmaz and co-workers developed anthracene and pyrene appended azo calix[4]arene 666 and 667 (see Scheme 18) and applied 666 in fluorescence imaging of Cu2+ in living cells [355]. The azo calix[4]arenes shown selective complexation to Cu2+ over other metal ions, which is revealed by UV–Vis and fluorescence spectroscopies. The binding constants are calculated as 2.34 × 103 and 7.51 × 103 M−1 for 666 and 667, respectively. Once incubated with 666 containing medium following Cu2+ treatment, the tested SW-620 cells showed obvious fluorescence (Fig. 20).
Reproduced with permission from Ref. [355]. Copyright 2016 from Elsevier
Fluorescence image and their corresponding bright-field transmission images. a Control cells (only cells without Cu2+or ligand 666); b fluorescence image of SW-620 cells after treatment with Cu2+and ligand 666; c merge view of bright field and fluorescence images.
Devices
In 1992, Tamaoki et al. synthesized and studied the isomerizations of azobenzenophane 1013 (see Scheme 21) in polycarbonate films through spectrophotometry [462]. The efficiency of photoisomerization of 1013 is dependent on the light intensity both in solution and on polymer film. This unique feature can be applied in the construction of photochromic memory with non-destructive read-out property (Fig. 21). The memory was written and read-out by exposure to 366 nm light at 5 mW cm−2 and 20 µW cm−2, respectively. The memory can be initialized by irradiating with light of wavelength longer than 450 nm.
Reprinted from Ref. [462]. Copyright 1992 with permission from Elsevier
Procedures for writing, monitoring and erasing of memories.
In 2006, Rouis et al. elaborated organic diodes based on sandwiching azo calix[4]arene layers between indium-thin oxide and Al contacts [282]. Optical and electrical properties of these devices were studied by current–voltage characteristics and electrical impedance spectroscopy in a wide frequency range. These materials displayed characteristic of semiconductors with energy band gaps in the range of 1.7–3 eV and the electrical characteristics follow a space charge limited conduction behavior. Authors also determined and fitted the relaxation frequencies of the hopping charge carriers.
Photocontrolled supramolecular catalysis
In 2003, Cacciapaglia et al. devised a photoswitchable supramolecular catalyst based on Ba2+ complex of azo bis(benzo-18-crown-6) ether 176 (see Scheme 5) to photocontrol the rate for ethanolysis of 4-carboxyacetanilides in basic solution (Fig. 22) [109]. Efficient ethanolysis requires the cooperation of two metal centers: one to bind the carboxylate group, and the other to deliver the alkoxide to the amide. The trans-azobenzene spacer is too extended to allow for proper two-point binding and cis-176 is efficient catalyst (kcis/ktrans up to 5), which is confirmed by molecular models. The catalytic activity could be reversibility switched in situ between ‘faster’ and ‘slower’ for several times by alternating exposure to UV or visible light.
Reproduced with permission from Ref. [109]. Copyright 2003 from American Chemical Society
Computer-generated structures of interswitchable trans and cis forms of 176·2[Ba2+].
Molecular machine
In 2006, Aida and co-workers achieved the coupling of several molecular motions in a light-powered system (Fig. 23) [507]. A photoresponsive host contain an azobenzene unit, a ferrocene unit as pivot, and two porphyrin units as binding sites. The host complexes with 4,4′-biisoquinoline guest with high binding constant. In the formed complex, the change in molecular shape on photoisomerization of the azobenzene is transmitted via rotation of ferrocene and ultimately induced the rotary motion in the guest. The author confirmed the motion by studying the chirality of the guest through circular dichroism spectra. The original state can be regenerated through irradiation with visible light. The system convert light energy into significant motion and larger system that could address remote control of molecular motion might be developed through similar strategy.
Reproduced with permission from Ref. [507]. Copyright 2006 from Nature Publishing Group
Design and concept of light-powered molecular pedal.
Others
In 2010, Haberhauer and Kallweit described the unidirectional photoisomerization process of in an azobenzene bearing macrocycle 1267 (Fig. 24) [575]. Trans- to cis-isomerization of azobenzene generates two enantiomeric cis-isomers with P or M chirality, respectively. For most of azobenzene derivatives the two enantiomeric isomers are energy equal and are in fast racemization. It is possible to switch the azobenzene unit unidirectionally by linking a chiral clamp. The irradiation with light of the achiral trans-isomer of 1267 gives rise to the cis-isomer with P helicity. The quantum mechanical computation revealed that the cis-(P) isomer of 1267 is much more stable than the cis-(M) isomer.
Reproduced with permission from Ref. [575]. Copyright 2010 from Wiley-VCH Verlag GmbH & Co. KGaA
Unidirectional switching of the cyclic azo macrocycle 1267.
In 2013, Deligöz and co-workers synthesized four azo calix[4]arene dyes for the application in dyeing fibers, including cotton, wool, acetate, polyether and polyamine [322]. Both perspiration fastness and water fastness of fibers dyed by these compounds are good. Furthermore, thermogravimetric analysis revealed that these dyes are all stable up to 245 °C, which can be effectively used in most kind of inks. It is worth mentioning that the tautomerization of these macrocycles need to be considered in the future.
Summary
Introducing azo groups into macrocycles can endow them with more intriguing chemical and physical properties, such as efficient recognition, guest induced color change for optical sensing, and photo-response. In this review, we first comprehensively summarized the structures of various macrocycles containing azo group. Most of popular macrocycles have many azo-modified derivatives, especially for crown ether and calixarene, due to the convenient synthesis of azo compounds and the facile modification of these macrocyclic scaffolds.
Furthermore, we reviewed several representative examples of these azo macrocycles for molecular recognition, self-assembly and application to give readers an impression of their properties and research status. In general, most works about azo macrocycles focused on their syntheses and (photo-responsive) model guest recognition. We listed > 1200 azo macrocyclic molecules but rarely found the works about application, and even self-assembly.
In our opinion, the supramolecular chemistry and application of azo macrocycles are still in their infancy and will develop flourishingly in the future since both azo compounds and macrocycles have high status in various fields. The breakthrough relies on finding methods to use both properties of azo compounds, such as photo- and redox-response, fast internal conversion and color, and unique supramolecular chemistry of each macrocycle. We have a vision that azo macrocycles will have more fascinating application in fields of diagnosis and therapy, molecular machine, liquid crystal and nonlinear optics. Its biomedical application, for example, tumor-selective imaging and targeting drug delivery based on hypoxia-responsive azo macrocycle, is of our particular interest in the near future.
References
Chmielewski, M.J., Jurczak, J.: Anion recognition by neutral macrocyclic amides. Chem. Eur. J. 11, 6080–6094 (2005)
Huang, W., Zhu, H.-B., Gou, S.-H.: Self-assembly directed by dinuclear zinc(II) macrocyclic species. Coord. Chem. Rev. 250, 414–423 (2006)
Zhang, X., Wang, C.: Supramolecular amphiphiles. Chem. Soc. Rev. 40, 94–101 (2011)
Jie, K., Zhou, Y., Yao, Y., Huang, F.: Macrocyclic amphiphiles. Chem. Soc. Rev. 44, 3568–3587 (2015)
Gibson, S.E., Lecci, C.: Amino acid derived macrocycles—an area driven by synthesis or application? Angew. Chem. Int. Ed. 45, 1364–1377 (2006)
Driggers, E.M., Hale, S.P., Lee, J., Terrett, N.K.: The exploration of macrocycles for drug discovery—an underexploited structural class. Nat. Rev. Drug Discov. 7, 608–624 (2008)
Marsault, E., Peterson, M.L.: Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery. J. Med. Chem. 54, 1961–2004 (2011)
Grave, C., Schlüter, A.D.: Shape-persistent, nano-sized macrocycles. Eur. J. Org. Chem. 2002, 3075–3098 (2002)
Zhao, D., Moore, J.S.: Shape-persistent arylene ethynylene macrocycles: syntheses and supramolecular chemistry. Chem. Commun. 7, 807–818 (2003)
Hoger, S.: Shape-persistent macrocycles: from molecules to materials. Chem. Eur. J. 10, 1320–1329 (2004)
Northrop, B.H., Chercka, D., Stang, P.J.: Carbon-rich supramolecular metallacycles and metallacages. Tetrahedron 64, 11495–11503 (2008)
Liu, Z., Nalluri, S.K.M., Stoddart, J.F.: Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes. Chem. Soc. Rev. 46, 2459–2478 (2017)
Yagai, S., Kitamura, A.: Recent advances in photoresponsive supramolecular self-assemblies. Chem. Soc. Rev. 37, 1520–1529 (2008)
Ma, X., Tian, H.: Bright functional rotaxanes. Chem. Soc. Rev. 39, 70–80 (2010)
Merino, E., Ribagorda, M.: Control over molecular motion using the cis-trans photoisomerization of the azo group. Beilstein J. Org. Chem. 8, 1071–1090 (2012)
Yasuda, S., Nakamura, T., Matsumoto, M., Shigekawa, H.: Phase switching of a single isomeric molecule and associated characteristic rectification. J. Am. Chem. Soc. 125, 16430–16433 (2003)
Beharry, A.A., Woolley, G.A.: Azobenzene photoswitches for biomolecules. Chem. Soc. Rev. 40, 4422–4437 (2011)
Kumar, G.S., Neckers, D.C.: Photochemistry of azobenzene-containing polymers. Chem. Rev. 89, 1915–1925 (1989)
Mukhopadhyay, R.D., Praveen, V.K., Ajayaghosh, A.: Photoresponsive metal–organic materials: exploiting the azobenzene switch. Mater. Horiz. 1, 572–576 (2014)
Yu, Y., Nakano, M., Ikeda, T.: Photomechanics: directed bending of a polymer film by light. Nature 425, 145 (2003)
Qu, D.H., Wang, Q.C., Zhang, Q.W., Ma, X., Tian, H.: Photoresponsive host-guest functional systems. Chem. Rev. 115, 7543–7588 (2015)
Reuter, R., Wegner, H.A.: Oligoazobenzenophanes—synthesis, photochemistry and properties. Chem. Commun. 47, 12267–12276 (2011)
Li, Z., Liang, J., Xue, W., Liu, G., Liu, S.H., Yin, J.: Switchable azo-macrocycles: from molecules to functionalisation. Supramol. Chem. 26, 54–65 (2013)
Wagner-Wysiecka, E., Lukasik, N., Biernat, J.F., Luboch, E.: Azo group(s) in selected macrocyclic compounds. J. Incl. Phenom. Macrocycl. Chem. 90, 189–257 (2018)
Pedersen, C.J.: The discovery of crown ethers. Science 241, 536 (1988)
Goldenberg, L.M., Denisov, N.N., Biernat, J.F.: Spectroscopic study of azo- and azoxycrowns binding with cations of similar ionic radius. J. Incl. Phenom. Macrocycl. Chem. 38, 171–186 (2000)
Luboch, E., Wagner-Wysiecka, E., Biernat, J.F.: Chromogenic azocrown ethers with peripheral alkyl, alkoxy, hydroxy or dimethylamino group. J. Supramol. Chem. 2, 279–291 (2002)
Luboch, E., Kravtsov, V.C.: Molecular structures and supramolecular architectures of two chromogenic 13-membered azobenzocrown ethers with a peripheral hydroxyl group in the benzene ring. J. Mol. Struct. 699, 9–15 (2004)
Luboch, E., Wagner-Wysiecka, E., Poleska-Muchlado, Z., Kravtsov, V.C.: Synthesis and properties of azobenzocrown ethers with π-electron donor, or π-electron donor and π-electron acceptor group(s) on benzene ring(s). Tetrahedron 61, 10738–10747 (2005)
Szarmach, M., Wagner-Wysiecka, E., Luboch, E.: Rearrangement of azoxybenzocrowns into chromophoric hydroxyazobenzocrowns and the use of hydroxyazobenzocrowns for the synthesis of ionophoric biscrown compounds. Tetrahedron 69, 10893–10905 (2013)
Goldenberg, L.M., Biernat, J.F., Petty, M.C.: Electro- and photochemistry of 13-membered azocrowns in solution and as Langmuir–Blodgett films. Langmuir 14, 1236–1241 (1998)
Goldenberg, L.M., Denisov, N.N., Biernat, J.F., Petty, M.C.: Electrochemical recognition properties of 13- and 16-membered azo- and azoxycrowns in solution. J. Electroanal. Chem. 509, 42–47 (2001)
Huesmann, H., Fujiwara, H., Luboch, E., Biernat, J.F., Möbius, D.: Influence of molecular organization of photo-active azo-phanes on the reactivity in monolayers at the air–water interface. J. Incl. Phenom. Macrocycl. Chem. 49, 181–185 (2004)
Kertmen, A., Szczygelska-Tao, J., Chojnacki, J.: Azo and azoxythiacrown ethers: synthesis and properties. Tetrahedron 69, 10662–10668 (2013)
Luboch, E., Wagner-Wysiecka, E., Rzymowski, T.: 4-Hexylresorcinol-derived hydroxyazobenzocrown ethers as chromoionophores. Tetrahedron 65, 10671–10678 (2009)
Wagner-Wysiecka, E., Szarmach, M., Chojnacki, J., Łukasik, N., Luboch, E.: Cation sensing by diphenyl-azobenzocrowns. J. Photochem. Photobiol. A Chem. 333, 220–232 (2017)
Zawisza, I., Bilewicz, R., Luboch, E., Biernat, J.F.: Langmuir–Blodgett films of azocrown ethers on electrodes—voltammetric recognition of isomers. J. Electroanal. Chem. 471, 156–166 (1999)
Zawisza, I., Bilewicz, R., Rosa Moncelli, M., Guidelli, R.: Electrochemistry of Langmuir–Blodgett and self-organized monolayers of an azocrown ether, both pure and mixed with a phospholipid. J. Electroanal. Chem. 509, 31–41 (2001)
Shimizu, F.M., Giacometti, J.A., Luboch, E., Biernat, J.F., Ferreira, M.: Preparation and characterization of Langmuir–Blodgett films of 16-membered azobenzocrown ether with naphthalene residue. Synth. Met. 159, 2378–2380 (2009)
Wagner-Wysiecka, E., Rzymowski, T., Szarmach, M., Fonari, M.S., Luboch, E.: Functionalized azobenzocrown ethers as sensor materials—the synthesis and ion binding properties. Sens. Actuator B 177, 913–923 (2013)
Skwierawska, A.M., Biernat, J.F., Kravtsov, V.C.: Synthesis and electrode properties of 19-membered azo- and azoxycrown ethers. Structure of dibenzo-19-azocrown-7. Tetrahedron 62, 149–154 (2006)
Tamaoki, N., Wada, M.: Dynamic control of racemization rate through E-Z photoisomerization of azobenzene and subsequent partial photoresolution under circular polarized light. J. Am. Chem. Soc. 128, 6284–6285 (2006)
Muszalska, E., Bilewicz, R.: Adsorptive stripping analysis and monolayer properties of crown ethers with an azo unit in the macrocycle. Analyst 119, 1235 (1994)
Miao, Y., Wang, X., Ouyang, D.: Theoretical study of crown ethers with incorporated azobenzene moiety. J. Mol. Model. 18, 963–972 (2012)
Luboch, E., Biernat, J.F., Muszalska, E., Bilewicz, R.: 13-Membered crown ethers with azo or azoxy unit in the macrocycle—synthesis, membrane electrodes, voltammetry and Langmuir monolayers. Supramol. Chem. 5, 201–210 (1995)
Zawisza, I., Bilewicz, R., Janus, K., Sworakowski, J., Luboch, E., Biernat, J.F.: Comparison of Z⇄E isomerization in Langmuir–Blodgett layers and in solution. Mater. Sci. Eng. C 22, 91–98 (2002)
Zawisza, I., Bilewicz, R., Luboch, E., Biernat, J.F.: Electrochemistry of azocrown ethers in Langmuir–Blodgett monolayers. Supramol. Chem. 12, 123–129 (2000)
Asakawa, M., Ashton, P.R., Balzani, V., Brown, C.L., Credi, A., Matthews, O.A., Newton, S.P., Raymo, F.M., Shipway, A.N., Spencer, N., Quick, A., Stoddart, J.F., White, A.J.P., Williams, D.J.: Photoactive azobenzene-containing supramolecular complexes and related interlocked molecular compounds. Chem. Eur. J. 5, 860–875 (1999)
Lyapunov, A., Kirichenko, T., Kulygina, C., Zubatyuk, R., Fonari, M., Kyrychenko, A., Doroshenko, A.: New fluorenonocrownophanes containing azobenzene: synthesis, properties and interaction with paraquat. J. Incl. Phenom. Macrocycl. Chem. 81, 499–508 (2015)
Luboch, E., Szarmach, M., Buczkowska, A., Wagner-Wysiecka, E., Kania, M., Danikiewicz, W.: Synthesis of thiol derivatives of azobenzocrown ethers. The preliminary studies on recognition of alkali metal ions by gold nanoparticles functionalized with azobenzocrown and lipoic acid. J. Incl. Phenom. Macrocycl. Chem. 83, 321–334 (2015)
Jablonowska, E., Palys, B., Wagner-Wysiecka, E., Jamrogiewicz, M., Biernat, J.F., Bilewicz, R.: pH-tunable equilibria in azocrown ethers with histidine moieties. Bioelectrochemistry 71, 99–106 (2007)
Anzai, J., Sakasegawa, S., Takemura, T., Osa, T.: Trans-cis isomerization of crown ether-substituted azobenzene amphiphiles in Langmuir–Blodgett membranes. Mater. Sci. Eng. C 2, 107–112 (1994)
Zawisza, I., Bilewicz, R., Luboch, E., Biernat, J.F.: Complexation of metal ions by azocrown ethers in Langmuir–Blodgett monolayers. J. Chem. Soc. Dalton Trans. 4, 499–503 (2000)
Tanigawa, I., Tsuemoto, K., Kaneda, T., Misumi, S.: Synthetic macrocyclic ligands. VI. Lithium ion-selectivefluorescent emission with crowned benzo- and naphtho-thiazolylphenols. Tetrahedron Lett. 25, 5327–5330 (1984)
Hashim, P.K., Thomas, R., Tamaoki, N.: Induction of molecular chirality by circularly polarized light in cyclic azobenzene with a photoswitchable benzene rotor. Chem. Eur. J. 17, 7304–7312 (2011)
Luboch, E., Jeszke, M., Szarmach, M., Lukasik, N.: New bis(azobenzocrown)s with dodecylmethylmalonyl linkers as ionophores for sodium selective potentiometric sensors. J. Incl. Phenom. Macrocycl. Chem. 86, 323–335 (2016)
Szczygelska-Tao, J., Biernat, J.F., Kravtsov, V.C., Simonov, Y.A.: Crown ethers with an azo or azoxy unit and sulfur atom(s) in a 13-membered macrocycle. Tetrahedron 55, 8433–8442 (1999)
Skwierawska, A., Luboch, E., Biernat, J.F., Kravtsov, V.C., Simonov, Y.A., Dvorkin, A.A., Bel’skii, V.K.: Stereochemistry of 16-membered azo- and azoxycrown ethers. Structures of their sandwich potassium iodide complexes. J. Incl. Phenom. Mol. Recognit. Chem. 31, 71–86 (1998)
Tahara, R., Morozumi, T., Nakamura, H., Shimomura, M.: Photoisomerization of azobenzocrown ethers. Effect of complexation of alkaline earth metal ions. J. Phys. Chem. B 101, 7736–7743 (1997)
Luboch, E., Biernat, J.F., Simonov, Y.A., Kravtsov, V.C., Bel’skii, V.K.: Structures of NaI complexes of 16-membered azo- and azoxycrown ethers. Correlation of crystal structure and carrier-doped membrane electrode selectivity. Supramol. Chem. 11, 109–118 (1999)
Sworakowski, J., Janusk, K., Nespurek, S.: Kinetics of photochemical reactions in condensed phases. What can be borrowed from methods of dielectric physics? IEEE Trans. Dielectr. Electr. Insul. 8, 543–548 (2001)
Janus, K., Koshets, I.A., Sworakowski, J., Nešpůrek, S.: An approximate non-isothermal method to study kinetic processes controlled by a distribution of rate constants: the case of a photochromic azobenzene derivative dissolved in a polymer matrix. J. Mater. Chem. 12, 1657–1663 (2002)
Janus, K., Sworakowski, J.: Photochromism of crown ethers with incorporated azobenzene moiety. J. Phys. Chem. B 109, 93–101 (2005)
Shimizu, F.M., Volpati, D., Giacometti, J.A., Sworakowski, J., Janus, K., Luboch, E.: Kinetics of photoinduced birefringence in the guest–host system of poly(methyl methacrylate) doped with azobenzene-containing crown ethers. J. Appl. Polym. Sci. 105, 130–136 (2007)
Fonari, M.S., Luboch, E., Collas, A., Bukrej, A., Blockhuys, F., Biernat, J.F.: Molecular structures of two E-azobenzocrown ethers. J. Mol. Struct. 892, 195–199 (2008)
Skwierawska, A., Biernat, J.F., Bilewicz, R.: 13-Membered azo- and azoxycrown compounds with sulfur atom in long side chain. Supramol. Chem. 12, 213–216 (2000)
Janus, K., Sworakowski, J., Luboch, E.: Kinetics of photochromic reactions in a 10-membered dibenzoazo crown ether. Chem. Phys. 285, 47–54 (2002)
Wygladacz, K., Malinowska, E., Szcztygelska-Tao, J., Biernat, J.F.: Azothia- and azoxythiacrown ethers as ion carriers. Part II. Anionic response of membrane electrodes. J. Incl. Phenom. Macrocycl. Chem. 39, 309–314 (2001)
Wygladacz, K., Malinowska, E., Szcztygelska-Tao, J., Biernat, J.F.: Azothia- and azoxythiacrown ethers as ion carriers. Part I. Cationic response of membrane electrodes. J. Incl. Phenom. Macrocycl. Chem. 39, 303–307 (2001)
Shiga, M., Nakamura, H., Takagi, M., Ueno, K.: Synthesis of azobenzo-crown ethers and their complexation behavior with metal ions. Bull. Chem. Soc. Jpn 57, 412–415 (1984)
Szczygelska-Tao, J., Biernat, J.F., Górski, Ł, Malinowska, E.: Studies on 16-membered azothia- and azoxythiacrown ethers as ion carriers in ion selective membranes. J. Incl. Phenom. Macrocycl. Chem. 49, 167–171 (2004)
Szczygelska-Tao, J., Fonari, M.S., Biernat, J.F.: Chromogenic azole diazothiacrown ethers. Supramol. Chem. 20, 651–658 (2008)
Wagner-Wysiecka, E., Skwierawska, A., Kravtsov, V.C., Biernat, J.F.: New class of chromogenic proton-dissociable azocrown reagents for alkali metal ions. J. Supramol. Chem. 1, 77–85 (2001)
Sadowska, K., Biernat, J.: Selective transport of Pb(II) across polymer inclusion membrane using imidazole azocrown ethers as carriers. Physicochem. Probl. MI 41, 133–143 (2007)
Ulewicz, M., Sadowska, K., Biernat, J.F.: Facilitated transport of Zn(II), Cd(II) and Pb(II) across polymer inclusion membranes doped with imidazole azocrown ethers. Desalination 214, 352–364 (2007)
Wagner-Wysiecka, E., Jamrógiewicz, M., Fonari, M.S., Biernat, J.F.: Azomacrocyclic derivatives of imidazole: synthesis, structure, and metal ion complexation properties. Tetrahedron 63, 4414–4421 (2007)
Ulewicz, M., Szczygelska-Tao, J., Biernat, J.F.: Selectivity of Pb(II) transport across polymer inclusion membranes doped with imidazole azothiacrown ethers. J. Membr. Sci. 344, 32–38 (2009)
Wagner-Wysiecka, E., Rzymowski, T., Fonari, M.S., Kulmaczewski, R., Luboch, E.: Pyrrole azocrown ethers—synthesis, crystal structures, and fluorescence properties. Tetrahedron 67, 1862–1872 (2011)
Luboch, E., Wagner-Wysiecka, E., Fainerman-Melnikova, M., Lindoy, L.F., Biernat, J.F.: Pyrrole azocrown ethers. Synthesis, complexation, selective lead transport and ion-selective membrane electrode studies. Supramol. Chem. 18, 593–601 (2006)
Luboch, E., Kravtsov, V.C., Konitz, A.: Reductive cyclization products of 1,2-bis(2-nitrophenoxy)ethanes. X-ray structures of 10-membered azoxycrown ether stereoisomers and the sodium iodide complex of a 20-membered azoazoxycrown. J. Supramol. Chem. 1, 101–110 (2001)
Shimizu, F.M., Ferreira, M., Constantino, C.J.L., Skwierawska, A.S., Biernat, J.F., Giacometti, J.A.: Fast dynamics in the optical storage with Langmuir–Blodgett films of a diazocrown ether molecule. J. Nanosci. Nanotechno. 8, 6367–6375 (2008)
Shimizu, F.M., Ferreira, M., Skwierawska, A.S., Biernat, J.F., Giacometti, J.A.: Spectroscopy and electrochemical characterization of Langmuir–Blodgett and physical vapor thin films of 29-membered diazocrown ether 1 with two n-octyl substituents. Synth. Met. 162, 995–999 (2012)
Wagner-Wysiecka, E., Luboch, E., Kowalczyk, M., Biernat, J.F.: Chromogenic macrocyclic derivatives of azoles—synthesis and properties. Tetrahedron 59, 4415–4420 (2003)
Inerowicz, H.D., Skwierawska, A., Biernat, J.F.: Novel chromogenic 21-membered azocrown ether lithium selective reagent. Supramol. Chem. 12, 111–114 (2000)
Inerowicz, H.D.: Lithium selective chromogenic azocrown ethers. J. Incl. Phenom. Macrocycl. Chem. 39, 211–214 (2001)
Szarmach, M., Wagner-Wysiecka, E., Fonari, M.S., Luboch, E.: Bis(azobenzocrown ether)s—synthesis and ionophoric properties. Tetrahedron 68, 507–515 (2012)
Pancur, T., Renth, F., Temps, F., Harbaum, B., Krüger, A., Herges, R., Näther, C.: Femtosecond fluorescence up-conversion spectroscopy of a rotation-restricted azobenzene after excitation to the S1 state. Phys. Chem. Chem. Phys. 7, 1985–1989 (2005)
Shinkai, S., Honda, Y., Ueda, K., Manabe, O.: Photoresponsive crown ethers. 12. Photocontrol of metal ion complexation with thiacrown ethers. Bull. Chem. Soc. Jpn. 57, 2144–2149 (1984)
Liu, M., Yan, X., Hu, M., Chen, X., Zhang, M., Zheng, B., Hu, X., Shao, S., Huang, F.: Photoresponsive host-guest systems based on a new azobenzene-containing cryptand. Org. Lett. 12, 2558–2561 (2010)
Shinkai, S., Honda, Y., Ueda, K., Manabe, O.: Photoresponsive crown ethers. Part 11. Azobenzene-pillared cylindrical macrocycle as a photoresponsive receptor. Isr. J. Chem. 24, 302–306 (1984)
Kim, J., Seo, E., Kim, S., Park, S., Kim, B.: Controllable movement of the azobenzene linked crown ether conjugated liposome. Sens. Actuator B 134, 843–848 (2008)
Shinkai, S., Honda, Y., Kusano, Y., Manabe, O.: A photoresponsive cylindrical ionophore. J. Chem. Soc. Chem. Commun. 15, 848 (1982)
Bencini, A., Bernardo, M.A., Bianchi, A., Ciampolini, M., Fusi, V., Nardi, N., Parola, A.J., Pina, F., Valtancoli, B.: Modulation of the ligational properties of a new cylindrical macrotricycle by coupling of photochemical- and pH-switching properties. J. Chem. Soc. Perkin Trans. 2 2, 413–418 (1998)
Shinkai, S., Honda, Y., Minami, T., Ueda, K., Manabe, O., Tashiro, M.: Photoresponsive crown ethers. 9. Cylindrical and phane crown ethers with azobenzene segments as a light-switch functional group. Bull. Chem. Soc. Jpn. 56, 1700–1704 (1983)
Bencini, A., Bianchi, A., Giorgi, C., Romagnoli, E., Lodeiro, C., Saint-Maurice, A., Pina, F., Valtancoli, B.: Photochemical- and pH-switching properties of a new photoelastic ligand based upon azobenzene. Basicity and anion binding. Supramol. Chem. 13, 277–285 (2006)
Kumano, A., Niwa, O., Kajiyama, T., Takayanagi, M., Kano, K., Shinkai, S.: Photoinduced ion permeation through ternary composite membrane composed of polymer/liquid crystal/azobenzene-bridged crown ether. Chem. Lett. 12, 1327–1330 (1983)
Shinkai, S., Shigematsu, K., Kusano, Y., Manabe, O.: Photoresponsive crown ethers. Part 3. Photocontrol of ion extraction and ion transport by several photofunctional bis(crown ethers). J. Chem. Soc. Perkin Trans. 1, 3279–3283 (1981)
Shinkai, S., Shigematsu, K., Honda, Y., Manabe, O.: Photoresponsive crown ethers. 13. Synthesis of photoresponsive NS2O crown ethers and application of the Cu(I) complexes to O2-binding. Bull. Chem. Soc. Jpn. 57, 2879–2884 (1984)
Shinkai, S., Ogawa, T., Kusano, Y., Manabe, O., Kikukawa, K., Goto, T., Matsuda, T.: Photoresponsive crown ethers. 4. Influence of alkali metal cations on photoisomerization and thermal isomerization of azobis(benzocrown ethers). J. Am. Chem. Soc. 104, 1960–1967 (1982)
Tohda, K., Yoshiyagawa, S., Kataoka, M., Odashima, K., Umezawa, Y.: Photoswitchable azobis(benzo-15-crown-5) ionophores as a molecular probe for phase boundary potentials at ion-selective poly(vinyl chloride) liquid membranes. Anal. Chem. 69, 3360–3369 (1997)
Dix, J.P., Vögtle, F.: Ligandstruktur und Komplexierung, L. Ionenselektive Farbstoffkronenether. Chem. Ber. 113, 457–470 (1980)
Anzai, J., Sasaki, H., Ueno, A., Osa, T.: Photo-induced potential changes across poly(vinyl chloride)–crown ether membranes. J. Chem. Soc. Chem. Commun. 18, 1045–1046 (1983)
Anzai, J., Ueno, A., Sasaki, H., Shimokawa, K., Osa, T.: Photocontrolled permeation of alkali cations through poly(vinyl chloride)/crown ether membrane. Makromol. Chem. Rapid Commun. 4, 731–734 (1983)
Anzai, J., Sasaki, H., Ueno, A., Osa, T.: Poly(vinyl chloride)/azobenzene-linked bis(15-crown-5) membranes. Photoinduced potential changes across asymmetric membranes. Chem. Lett. 13, 1205–1208 (1984)
Anzai, J., Sasaki, H., Ueno, A., Osa, T.: Photoinduced membrane potential changes. Poly(vinyl chloride) membranes entrapping a photoresponsive bis-(15-crown-5) derivative. J. Chem. Soc. Perkin Trans. 2 7, 903–907 (1985)
Anzai, J.-I., Sasaki, H., Ueno, A., Osa, T.: Photoinduced membrane potential changes. Bi-ionic potential across poly(vinyl chloride) membranes entrapping a photoresponsive bis(15-crown-5) derivative and the effects of photoirradiation. J. Polym. Sci. A 24, 681–689 (1986)
Pang, J., Ye, Y., Tian, Z., Pang, X., Wu, C.: Theoretical insight into azobis-(benzo-18-crown-6) ether combined with the alkaline earth metal cations. Comput. Theor. Chem. 1066, 28–33 (2015)
Kitazawa, S., Kimura, K., Shono, T.: Bis(crown ether) dyes incorporating azophenol structure. Bull. Chem. Soc. Jpn 56, 3253–3257 (1983)
Cacciapaglia, R., Di Stefano, S., Mandolini, L.: The bis-barium complex of a butterfly crown ether as a phototunable supramolecular catalyst. J. Am. Chem. Soc. 125, 2224–2227 (2003)
Kimura, K., Hirao, M., Yokoyama, M.: Synthesis of a crowned azobenzene liquid crystal and its application to thermoresponsive ion-conducting films. J. Mater. Chem. 1, 293 (1991)
Hirose, K.: A practical guide for the determination of binding constants. J. Incl. Phenom. Macrocycl. Chem. 39, 193–209 (2001)
Dix, J.P., Vögtle, F.: Ion-selective crown ether dyes. Angew. Chem. Int. Ed. 17, 857–859 (1978)
Kimura, K., Tanaka, M., Iketani, S., Shono, T.: Synthesis and cation-extraction study of lithium-selective chromogenic 14-crown-4 derivatives. J. Org. Chem. 52, 836–844 (1987)
Shinkai, S., Ishihara, M., Ueda, K., Manabe, O.: Photoresponsive crown ethers. Part 14. Photoregulated crown–metal complexation by competitive intramolecular tail(ammonium)-biting. J. Chem. Soc. Perkin Trans. 2 4, 511–518 (1985)
Naemura, K., Matsunaga, K., Fuji, J., Ogasahara, K., Nishikawa, Y., Hirose, K., Tobe, Y.: Temperature dependence of enantioselectivity in complexations of optically active phenolic crown ethers with chiral amines in solution. Anal. Sci. 14, 175–182 (1998)
Kaneda, T., Ishizaki, Y., Misumi, S., Kai, Y., Hirao, G., Kasai, N.: Synthesis, coloration, and crystal structure of the dibasic chromoacerand-piperazine 1:1 salt complex. J. Am. Chem. Soc. 110, 2970–2972 (1988)
Misumi, S., Kaneda, T.: Cation selective complexation-coloration with chromophoric crowns. J. Incl. Phenom. Mol. Recognit. Chem. 7, 83–90 (1989)
Shinkai, S., Ishihara, M., Manabe, O.: Photoresponsive crown ethers. XVII. Metal extraction with a polymer bearing pendent photoresponsive crown ethers. Polym. J. 17, 1141–1144 (1985)
Shinkai, S., Miyazaki, K., Manabe, O.: Photoresponsive crown ethers. Part 18. Photochemically ‘switched-on’ crown ethers containing an intra-annular azo substituent and their application to membrane transport. J. Chem. Soc. Perkin Trans. 1, 449–456 (1987)
King, A.M., Moore, C.P., Sandanayake, K.R.A.S., Sutherland, I.O.: A highly selective chromoionophore for potassium based upon a bridged calix[4]arene. J. Chem. Soc. Chem. Commun. 7, 582–584 (1992)
Anzai, J., Ueno, A., Osa, T.: Photo-excitable membranes. Photoinduced membrane potential changes across poly(vinyl chloride) membranes doped with azobenzene-modified crown ethers. J. Chem. Soc. Perkin Trans. 2 1, 67–71 (1987)
Anzai, J.-I., Hasebe, Y., Ueno, A., Osa, T.: Photoexcitable polymer membranes. Photoinduced membrane potential across poly(vinyl chloride) membrane doped with a photosensitive crown ether having lipophilic side chain. J. Polym. Sci. A 26, 1519–1529 (1988)
Akabori, S., Miura, Y., Yotsumoto, N., Uchida, K., Kitano, M., Habata, Y.: Synthesis of photoresponsive crown ethers having a phosphoric acid functional group as anionic cap and their selective complexing abilities toward alkali metal cations. J. Chem. Soc. Perkin Trans. 1 20, 2589–2594 (1995)
Cho, E.N., Li, Y., Kim, H.J., Hyun, M.H.: A colorimetric chiral sensor based on chiral crown ether for the recognition of the two enantiomers of primary amino alcohols and amines. Chirality 23, 349–353 (2011)
Merten, C., Hyun, M.H., Xu, Y.: Absolute configuration and predominant conformations of a chiral crown ether-based colorimetric sensor: a vibrational circular dichroism spectroscopy and DFT study of chiral recognition. Chirality 25, 294–300 (2013)
Razus, A.C., Birzan, L., Tecuceanu, V., Cristea, M., Hanganu, A.: Benzo-and dibenzo-crown ethers substituted with (azulene-1-yl) azo chromophores. Synthesis and properties. Rev. Roum. Chim. 57, 987–995 (2012)
Yamashita, T., Nakamura, H., Takagi, M., Ueno, K.: Synthesis of crown ether dyes. Bull. Chem. Soc. Jpn 53, 1550–1554 (1980)
Shinkai, S., Minami, T., Kusano, Y., Manabe, O.: Photoresponsive crown ethers. 5. Light-driven ion transport by crown ethers with a photoresponsive anionic cap. J. Am. Chem. Soc. 104, 1967–1972 (1982)
Naemura, K., Takeuchi, S., Asada, M., Hirose, K., Tobe, Y., Kaneda, T., Sakata, Y.: The synthesis of azophenolic crown ethers of Cs symmetry incorporating cis-1-phenylcyclohexane-1,2-diol residues and diastereotopic face selectivity in complexation of ethanolamine by their diastereotopic faces. J. Chem. Soc. Chem. Commun. 6, 711–712 (1994)
Naemura, K., Takeuchi, S., Asada, M., Ueno, K., Hirose, K., Tobe, Y., Kaneda, T., Sakata, Y.: Synthesis of azophenolic crown ethers of Cs symmetry incorporating cis-1-phenylcyclohexane-1,2-diol residues as a steric barrier and diastereotopic face selectivity in complexation of amines by their diastereotopic faces. J. Chem. Soc. Perkin Trans. 1 11, 1429–1435 (1995)
Naemura, K., Ueno, K., Takeuchi, S., Hirose, K., Tobe, Y., Kaneda, T., Sakata, Y.: Preparation and enantiomer recognition behaviour of azophenolic crown ethers containing cis-1-phenylcyclohexane-l,2-diol as the chiral subunit and 2,4-dinitrophenylazophenol as the chromophore. J. Chem. Soc. Perkin Trans. 1 4, 383–388 (1996)
Naemura, K., Ueno, K., Takeuchi, S., Tobe, Y., Kaneda, T., Sakata, Y.: Azophenolic acerands having chiral 1-phenyl-cis-1,2-cyclohexanediol units: a correlation between enantiorecognitive coloration and host-guest complementarity. J. Am. Chem. Soc. 115, 8475–8476 (1993)
Kimura, K., Mizutani, R., Suzuki, T., Yokoyama, M.: Photochemical ionic-conductivity switching systems of photochromic crown ethers for information technology. J. Incl. Phenom. Mol. Recognit. Chem. 32, 295–310 (1998)
Al-Amir, S.M.S., Ashworth, D.C., Narayanaswamy, R., Moss, R.E.: Synthesis and characterization of some chromogenic crown ethers as potential optical sensors for potassium ions. Talanta 36, 645–650 (1989)
Chun, K., Kim, T.H., Lee, O.S., Hirose, K., Chung, T.D., Chung, D.S., Kim, H.: Structure-selective recognition by voltammetry: enantiomeric determination of amines using azophenolic crowns in aprotic solvent. Anal. Chem. 78, 7597–7600 (2006)
Nakamura, H., Nishida, H., Takagi, M., Ueno, K.: Chromogenic crown ether reagents for spectrophotometric determinations of sodium and potassium. Anal. Chim. Acta 139, 219–227 (1982)
Katayama, Y., Nita, K., Ueda, M., Nakamura, H., Takagi, M., Ueno, K.: Synthesis of chromogenic crown ethers and liquid–liquid extraction of alkali metal ions. Anal. Chim. Acta 173, 193–209 (1985)
Kimura, K., Hirao, M., Tokuhisa, H., Yokoyama, M.: Cation-complexation-induced aggregation and specific ion conduction of lipophilic crowned azobenzenes. J. Incl. Phenom. Mol. Recognit. Chem. 13, 273–285 (1992)
Naemura, K., Asada, M., Hirose, K., Tobe, Y.: Preparation and enantiomer recognition of chiral azophenolic crown ethers having three chiral barriers on each of the homotopic faces. Tetrahedron: Asymmetry 6, 1873–1876 (1995)
Nakashima, K., Nakatsuji, S.I., Akiyama, S., Kaneda, T., Misumi, S.: The complexation of “crowned” 4-(2,4-dinitrophenylazo)phenol with alkali and alkaline earth metal ions, and its application to the determination of Li(I) in a pharmaceutical preparation. Chem. Pharm. Bull. 34, 168–173 (1986)
Chapoteau, E., Czech, B.P., Gebauer, C.R., Kumar, A., Leong, K., Mytych, D.T., Zazulak, W., Desai, D.H., Luboch, E.: Phenylazophenol-quinone phenylhydrazone tautomerism in chromogenic cryptands and corands with inward-facing phenolic units and their acyclic analogs. J. Org. Chem. 56, 2575–2579 (1991)
Kaneda, T., Sugihara, K., Kamiya, H., Misumi, S.: Synthetic macrocyclic ligands. IV. Lithium ion-characteristic coloration of a “crowned” dinitrophenylazophenol. Tetrahedron Lett. 22, 4407–4408 (1981)
Misumi, S., Sugihara, K., Kaneda, T.: Synthetic macrocyclic ligands. V. “Crowned” dinitrophenylazophenols: dissolving and colorating agent of alkali and alkaline earth metal salts in organic solvents. Heterocycles 18, 57 (1982)
Nakashima, K., Nakatsuji, S.i., Akiyama, S., Kaneda, T., Misumi, S.: A new method for the spectrophotometric determination of Li(I) with a “crowned” dinitrophenylazophenol. Chem. Lett. 11, 1781–1782 (1982)
Nakashima, K., Nakatsuji, S.i., Akiyama, S., Tanigawa, I., Kaneda, T., Misumi, S.: A sensitive method for the fluorometric determination of lithium with a “crowned” benzothiazolylphenol. Talanta 31, 749–751 (1984)
Nakashima, K., Nagaoka, Y., Nakatsuji, S.i., Kaneda, T., Tanigawa, I., Hirose, K., Misumi, S., Akiyama, S.: Fluorescence reactions of “crowned” benzothiazolylphenols with alkali and alkaline earth metal ions and their analytical applications. Bull. Chem. Soc. Jpn. 60, 3219–3223 (1987)
Jung, J.H., Lee, S.J., Kim, J.S., Lee, W.S., Sakata, Y., Kaneda, T.: Alpha-CD/crown-appended diazophenol for selective sensing of amines. Org. Lett. 8, 3009–3012 (2006)
Jung, J.H., Lee, H.Y., Jung, S.H., Lee, S.J., Sakata, Y., Kaneda, T.: A color version of the Hinsberg test: permethylated cyclodextrin and crown-appended azophenol for highly selective sensing of amines. Tetrahedron 64, 6705–6710 (2008)
Kim, J.K., Song, S.H., Kim, J.H., Kim, T.H., Kim, H.S., Suh, H.S.: Synthesis of chiral azophenolic pyridino-18-crown-6 ether and its enantiomeric recognition toward chiral primary amines. Bull. Korean Chem. Soc. 27, 1577–1580 (2006)
Tokuhisa, H., Yokoyama, M., Kimura, K.: Photoinduced switching of ionic conductivity by metal ion complexes of vinyl copolymers carrying crowned azobenzene and biphenyl moieties at the side chain. J. Mater. Chem. 8, 889–891 (1998)
Tokuhisa, H., Yokoyama, M., Kimura, K.: Photoresponsive ion-conducting behavior of polysiloxanes carrying a crowned azobenzene moiety at the side chain. Macromolecules 27, 1842–1846 (1994)
Shinkai, S., Nakaji, T., Nishida, Y., Ogawa, T., Manabe, O.: Photoresponsive crown ethers. 1. Cis-trans isomerism of azobenzene as a tool to enforce conformational changes of crown ethers and polymers. J. Am. Chem. Soc. 102, 5860–5865 (1980)
Tokuhisa, H., Yokoyama, M., Kimura, K.: Synthesis of vinyl polymers incorporating different crowned azobenzene moieties and their application to photoresponsive ion-conducting system. Bull. Chem. Soc. Jpn. 69, 2123–2130 (1996)
Iftime, M., Ardeleanu, R., Fifere, N., Airinei, A., Cozan, V., Bruma, M.: New copoly(ether sulfone)s containing azobenzene crown-ether and fluorene moieties. Dyes Pigm. 106, 111–120 (2014)
Ardeleanu, R., Airinei, A., Sacarescu, G., Sacarescu, L.: Photosensitive crown ether–siloxane copolymers bearing azobenzene chromophores. Eur. Polym. J. 38, 2265–2270 (2002)
Harikrishnan, U., Menon, S.K.: The synthesis, characterization and spectral properties of crown ether based disazo dyes. Dyes Pigm. 77, 462–468 (2008)
Uma, H.K., Menon, S.K.: Crown ether bis-diazo dyes for aqueous inkjet inks by micro emulsion technique. Proced. Eng. 51, 436–442 (2013)
Pandya, B.R., Agrawal, Y.K.: Synthesis and characterisation of crown ether based azo dyes. Dyes Pigm. 52, 161–168 (2002)
Micheloni, M., Formica, M., Fusi, V., Romani, P., Pontellini, R., Dapporto, P., Paoli, P., Rossi, P., Valtancoli, B.: Synthesis, crystal structures and lithium encapsulation by some phenolic aza cages. Eur. J. Inorg. Chem. 2000, 51–57 (2000)
Zazulak, W., Chapoteau, E., Czech, B.P., Kumar, A.: Novel cryptand chromoionophores for determination of lithium ions. J. Org. Chem. 57, 6720–6727 (1992)
Chapoteau, E., Czech, B.P., Zazulak, W., Kumar, A.: First practical colorimetric assay of lithium in serum. Clin. Chem. 38, 1654–1657 (1992)
Shinkai, S., Kinda, H., Manabe, O.: Photoresponsive complexation of metal cations with an azobenzene-crown-azobenzene bridge immobilized in polymer supports. J. Am. Chem. Soc. 104, 2933–2934 (1982)
Shinkai, S., Kinda, H., Ishihara, M., Manabe, O.: Photoresponsive crown ethers. 10. Metal complexation by light-switched crown ethers immobilized in polymer matrices. J. Polym. Sci. Polym. Chem. Ed. 21, 3525–3539 (1983)
Arima, H., Hayashi, Y., Higashi, T., Motoyama, K.: Recent advances in cyclodextrin delivery techniques. Expert Opin. Drug Deliv. 12, 1425–1441 (2015)
Ueno, A., Kuwabara, T., Nakamura, A., Toda, F.: A modified cyclodextrin as a guest responsive colour-change indicator. Nature 356, 136–137 (1992)
Kuwabara, T., Nakamura, A., Ueno, A., Toda, F.: Inclusion complexes and guest-induced color changes of pH-indicator-modified beta-cyclodextrins. J. Phys. Chem. 98, 6297–6303 (1994)
Kuwabara, T., Nakamura, A., Ueno, A., Toda, F.: Supramolecular thermochromism of a dye-appended β-cyclodextrin. J. Chem. Soc. Chem. Commun. 6, 689–690 (1994)
Kuwabara, T., Nakajima, H., Nanasawa, M., Ueno, A.: Color change indicators for molecules using methyl red-modified cyclodextrins. Anal. Chem. 71, 2844–2849 (1999)
Kuwabara, T., Aoyagi, T., Takamura, M., Matsushita, A., Nakamura, A., Ueno, A.: Heterodimerization of Dye-modified cyclodextrins with native cyclodextrins. J. Org. Chem. 67, 720–725 (2002)
Kuwabara, T., Sugiyama, K.: Hyperchromisity and molecular recognition of a novel modified beta-cyclodextrin tethering with phenylaminoazobenzene. Anal. Sci. 29, 905–909 (2013)
Casas-Solvas, J.M., Martos-Maldonado, M.C., Vargas-Berenguel, A.: Synthesis of β-cyclodextrin derivatives functionalized with azobenzene. Tetrahedron 64, 10919–10923 (2008)
Liu, Y., Yang, Z.X., Chen, Y.: Syntheses and self-assembly behaviors of the azobenzenyl modified beta-cyclodextrins isomers. J. Org. Chem. 73, 5298–5304 (2008)
Jog, P.V., Gin, M.S.: A light-gated synthetic ion channel. Org. Lett. 10, 3693–3696 (2008)
Ueno, A., Fukushima, M., Osa, T.: Inclusion complexes and Z–E photoisomerization of β-cyclodextrin bearing an azobenzene pendant. J. Chem. Soc. Perkin Trans. 2 7, 1067–1072 (1990)
Ueno, A., Tomita, Y., Osa, T.: Photoresponsive binding ability of azobenzene-appended γ-cyclodextrin. Tetrahedron Lett. 24, 5245–5248 (1983)
Ncube, P., Krause, R.W., Mamba, B.B.: Fluorescent sensing of chlorophenols in water using an azo dye modified beta-cyclodextrin polymer. Sensors 11, 4598–4608 (2011)
Fukushima, M., Osa, T., Ueno, A.: Photocontrol of molecular association attained by azobenzene-modified cyclodextrin. J. Chem. Soc. Chem. Commun. 1, 15 (1991)
Fujimoto, T., Sakata, Y., Kaneda, T.: The first competitive formation of [4] and [2]supercyclodextrins by self-association of an α-cyclodextrin bearing a bisazophenol group. Chem. Lett. 29, 764–765 (2000)
Lee, W.-S., Ueno, A.: Photocontrol of the catalytic activity of a β-cyclodextrin bearing azobenzene and histidine moieties as a pendant group. Macromol. Rapid Commun. 22, 448–450 (2001)
Di Motta, S., Avellini, T., Silvi, S., Venturi, M., Ma, X., Tian, H., Credi, A., Negri, F.: Photophysical properties and conformational effects on the circular dichroism of an azobenzene-cyclodextrin [1]rotaxane and its molecular components. Chem. Eur. J. 19, 3131–3138 (2013)
Fukushima, M., Osa, T., Ueno, A.: Photoswitchable multi-response sensor of azobenzene-modified γ-cyclodextrin for detecting organic compounds. Chem. Lett. 20, 709–712 (1991)
Fujimoto, T., Sakata, Y., Kaneda, T.: The first Janus [2]rotaxane. Chem. Commun. 21, 2143–2144 (2000)
Liu, Y., Zhao, Y.-L., Zhang, H.-Y., Fan, Z., Wen, G.-D., Ding, F.: Spectrophotometric study of inclusion complexation of aliphatic alcohols by β-cyclodextrins with azobenzene tether. J. Phys. Chem. B 108, 8836–8843 (2004)
Ueno, A., Moriwaki, F., Osa, T., Hamada, F., Murai, K.: Association, photodimerization, and induced-fit types of host-guest complexation of anthracene-appended gamma-cyclodextrin derivatives. J. Am. Chem. Soc. 110, 4323–4328 (1988)
Fujimoto, T., Uejima, Y., Imaki, H., Kawarabayashi, N., Jung, J.H., Sakata, Y., Kaneda, T.: The first lipophilic face-to-face dimers of permethylated α-cyclodextrin-azobenzene dyads through a p-xylylene spacer. Chem. Lett. 29, 564–565 (2000)
Kuwabara, T., Shiba, K., Ozawa, M., Miyajima, N., Suzuki, Y.: Synthesis and different molecular recognition of two dye-modified cyclodextrins with spacer of different length. Tetrahedron Lett. 47, 4433–4436 (2006)
Kuwabara, T., Shiba, K., Nakajima, H., Ozawa, M., Miyajima, N., Hosoda, M., Kuramoto, N., Suzuki, Y.: Host-guest complexation affected by pH and length of spacer for hydroxyazobenzene-modified cyclodextrins. J. Phys. Chem. A 110, 13521–13529 (2006)
Cao, J., Ma, X., Min, M., Cao, T., Wu, S., Tian, H.: INHIBIT logic operations based on light-driven beta-cyclodextrin pseudo[1]rotaxane with room temperature phosphorescence addresses. Chem. Commun. 50, 3224–3226 (2014)
Ueno, A., Saka, R., Osa, T.: One host-two guests complexation of photosensitive capped cyclodextrin with amino acids. Chem. Lett. 8, 841–844 (1979)
Ueno, A., Saka, R., Osa, T.: Conformational change of photoresponsive capped cyclodextrin detected by circular dichroism. Chem. Lett. 8, 1007–1010 (1979)
Ueno, A., Yoshimura, H., Saka, R., Osa, T.: Photocontrol of binding ability of capped cyclodextrin. J. Am. Chem. Soc. 101, 2779–2780 (1979)
Ueno, A., Saka, R., Osa, T.: Interactions of organic solvents with photoresponsive capped cyclodextrin in aqueous solution. Chem. Lett. 9, 29–32 (1980)
Ueno, A., Takahashi, K., Osa, T.: Photocontrol of catalytic activity of capped cyclodextrin. J. Chem. Soc. Chem. Commun. 3, 94 (1981)
Fujita, K., Fujiwara, S., Yamada, T., Tsuchido, Y., Hashimoto, T., Hayashita, T.: Design and function of supramolecular recognition systems based on guest-targeting probe-modified cyclodextrin receptors for ATP. J. Org. Chem. 82, 976–981 (2017)
Inoue, Y., Kuad, P., Okumura, Y., Takashima, Y., Yamaguchi, H., Harada, A.: Thermal and photochemical switching of conformation of poly(ethylene glycol)-substituted cyclodextrin with an azobenzene group at the chain end. J. Am. Chem. Soc. 129, 6396–6397 (2007)
Ncube, P., Krause, R.W.M., Mamba, B.B.: Detection of chloroform in water using an azo dye-modified β-cyclodextrin—epichlorohydrin copolymer as a fluorescent probe. Phys. Chem. Earth 67–69, 79–85 (2014)
Ma, X., Qu, D., Ji, F., Wang, Q., Zhu, L., Xu, Y., Tian, H.: A light-driven [1]rotaxane via self-complementary and Suzuki-coupling capping. Chem. Commun. 14, 1409–1411 (2007)
Ma, X., Wang, Q., Tian, H.: Disparate orientation of [1]rotaxanes. Tetrahedron Lett. 48, 7112–7116 (2007)
Guo, H., Yang, J., Zhou, J., Zeng, L., Zhao, L., Xu, B.: Photoresponsive self-assembly of a β-cyclodextrin derivative with an azobenzene terminal group in water. Dyes Pigm. 149, 626–632 (2018)
Aoyagi, T., Nakamura, A., Ikeda, H., Ikeda, T., Mihara, H., Ueno, A.: Alizarin yellow-modified β-cyclodextrin as a guest-responsive absorption change sensor. Anal. Chem. 69, 659–663 (1997)
Nakagama, T., Hirasawa, K., Uchiyama, K., Hobo, T.: Photo-responsive retention behavior of azobenzene-modified cyclodextrin stationary phase in micro-HPLC. Anal. Sci. 17, 119–124 (2001)
Nakagama, T., Yamaguchi, A., Hirasawa, K., Yoshida, K., Uchiyama, K., Hobo, T.: Photo-response assisted enantiomer separations on an azobenzene-modified gamma-cyclodextrin stationary phase in micro-HPLC. Anal. Sci. 18, 49–53 (2002)
Casas-Solvas, J.M., Vargas-Berenguel, A.: Synthesis of a β-cyclodextrin derivative bearing an azobenzene group on the secondary face. Tetrahedron Lett. 49, 6778–6780 (2008)
Aoyagi, T., Ueno, A., Fukushima, M., Osa, T.: Synthesis and photoisomerization of an azobenzene derivative bearing two β-cyclodextrin units at both ends. Macromol. Rapid Commun. 19, 103–105 (1998)
Anand, R., Manoli, F., Vargas-Berenguel, A., Monti, S.: Photocontrolled binding of artemisinin to a bis(β-cyclodextrin) bearing azobenzene on the primary face. J. Drug Deliv. Sci. Technol. 22, 266–269 (2012)
Kikuchi, T., Narita, M., Hamada, F.: Synthesis of bis dansyl-modified β-cyclodextrin dimer linked with azobenzene and its fluorescent molecular recognition. J. Incl. Phenom. Macrocycl. Chem. 44, 329–334 (2002)
Sun, H.L., Chen, Y., Zhao, J., Liu, Y.: Photocontrolled reversible conversion of nanotube and nanoparticle mediated by beta-cyclodextrin dimers. Angew. Chem. Int. Ed. 54, 9376–9380 (2015)
Sun, H.L., Chen, Y., Han, X., Liu, Y.: Tunable supramolecular assembly and photoswitchable conversion of cyclodextrin/diphenylalanine-based 1D and 2D nanostructures. Angew. Chem. Int. Ed. 56, 7062–7065 (2017)
Liu, Y., Kang, S., Chen, Y., Yang, Y.-W., Huskens, J.: Photo-induced switchable binding behavior of bridged bis(β-cyclodextrin) with an azobenzene dicarboxylate linker. J. Incl. Phenom. Macrocycl. Chem. 56, 197–201 (2006)
Ma, H., Wang, F., Li, W., Ma, Y., Yao, X., Lu, D., Yang, Y., Zhang, Z., Lei, Z.: Supramolecular assemblies of azobenzene-β-cyclodextrin dimers and azobenzene modified polycaprolactones. J. Phys. Org. Chem. 27, 722–728 (2014)
Hamon, F., Blaszkiewicz, C., Buchotte, M., Banaszak-Leonard, E., Bricout, H., Tilloy, S., Monflier, E., Cezard, C., Bouteiller, L., Len, C., Djedaini-Pilard, F.: Synthesis and characterization of a new photoinduced switchable beta-cyclodextrin dimer. Beilstein J. Org. Chem. 10, 2874–2885 (2014)
Gao, C., Ma, X., Zhang, Q., Wang, Q., Qu, D., Tian, H.: A light-powered stretch-contraction supramolecular system based on cobalt coordinated [1]rotaxane. Org. Biomol. Chem. 9, 1126–1132 (2011)
Volker, B.: Calixarenes, macrocycles with (almost) unlimited possibilities. Angew. Chem. Int. Ed. 34, 713–745 (1995)
Gutsche, C.D., Dhawan, B., Levine, J.A., Hyun No, K., Bauer, L.J.: Calixarenes 9: conformational isomers of the ethers and esters of calix[4]arene. Tetrahedron 39, 409–426 (1983)
Sener, N., Eriskin, S., Gur, M., Sener, I.: Novel disubstituted calix[4]arenes containing chromogenic groups on the lower rim: synthesis, structural identification, and absorption properties. J. Heterocycl. Chem. 55, 988–994 (2018)
Vögtle, F., Udelhofen, D., Abramson, S., Fuchs, B.: Photoresponsive lower-rim azobenzene substituted and bridged calix[4]arenes. J. Photochem. Photobiol. A 131, 41–48 (2000)
Sutariya, P.G., Modi, N.R., Pandya, A., Rana, V.A., Menon, S.K.: Synthesis, mesomorphism and dielectric behaviour of novel basket shaped scaffolds constructed on lower rim azocalix[4]arenes. RSC Adv. 3, 4176 (2013)
McCarrick, M., Harris, S.J., Diamond, D.: Assessment of three azophenol calix[4]arenes as chromogenic ligands for optical detection of alkali metal ions. Analyst 118, 1127 (1993)
An, L., Wang, M.-H.: Novel synthesis of calix[n]arene amidoazobenzene derivatives. J. Chem. Res. 2006, 75–77 (2006)
McCarrick, M., Harris, S.J., Diamond, D.: Assessment of a chromogenic calix[4]arene for the rapid colorimetric detection of trimethylamine. J. Mater. Chem. 4, 217 (1994)
Vavilova, A.A., Nosov, R.V., Yakimova, L.S., Antipin, I.S., Stoikov, I.I.: Synthesis of photo-switchable derivatives of p-tert-butyl thiacalix[4]arenes containing ethoxycarbonyl and 4-amidoazobenzene fragments in the lower rim substituents. Macroheterocycles 6, 219–226 (2013)
Liu, Y., Wang, H., Zhang, H.Y., Liang, P.: A metallo-capped polyrotaxane containing calix[4]arenes and cyclodextrins and its highly selective binding for Ca2+. Chem. Commun. 10, 2266–2267 (2004)
Gong, L., Gong, S., Dong, H., Zhang, C., Chen, Y.: Liquid crystalline behavior and fluorescent property of calix[4]arene containing azobenzene photochromic group. Front. Chem. 2, 292–295 (2007)
Shaabani, B., Shaghaghi, Z., Khandar, A.A.: Optical spectroscopy studies of the complexation of bis(azophenol)calix[4]arene possessing chromogenic donors with Ni2+, Co2+, Cu2+, Pb2+ and Hg2+. Spectrochim. Acta A 98, 81–85 (2012)
Kubinyi, M., Pal, K., Baranyai, P., Grofcsik, A., Bitter, I., Grun, A.: Absorption, fluorescence, and CD spectroscopic study of chiral recognition by a binaphthyl-derived chromogenic calixcrown host. Chirality 16, 174–179 (2004)
Lee, H.K., Yeo, H., Park, D.H., Jeon, S.: Synthesis of azo-functionalized calix[4]arenes and its application to chloride-selective electrode as ionophores. Bull. Korean Chem. Soc. 24, 1737–1741 (2003)
Saadioui, M., Asfari, Z., Vicens, J., Reynier, N., Dozol, J.F.: Synthesis, characterisation and uv-vis properties of azocalix[4]crowns. J. Incl. Phenom. Mol. Recognit. Chem. 28, 223–244 (1997)
Consoli, G.M.L., Geraci, C., Neri, P., Bergamini, G., Balzani, V.: Azobenzene-bridged calix[8]arenes. Tetrahedron Lett. 47, 7809–7813 (2006)
Pipoosananakaton, B., Sukwattanasinitt, M., Jaiboon, N., Chaichit, N., Tuntulan, T.: New azobenzene crown p-tert-butylcalix[4]arenes as switchable receptors for ions: synthesis and isomerization studies. Bull. Korean Chem. Soc. 21, 867–874 (2000)
Pipoosananakaton, B., Sukwattanasinitt, M., Jaiboon, N., Chaichit, N., Tuntulani, T.: Preparation of new azobenzene crown ether p-tert-butylcalix[4]arenes and their roles as switchable ionophores for Na+ and K+ ions. Tetrahedron Lett. 41, 9095–9100 (2000)
Rojanathanes, R., Pipoosananakaton, B., Tuntulani, T., Bhanthumnavin, W., Orton, J.B., Cole, S.J., Hursthouse, M.B., Grossel, M.C., Sukwattanasinitt, M.: Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix[4]arene. Tetrahedron 61, 1317–1324 (2005)
Park, S.J., Choe, J.I.: DFT study for azobenzene crown ether p-tert-butylcalix[4]arene complexed with alkali metal ion. Bull. Korean Chem. Soc. 29, 541–545 (2008)
Galan, H., Hennrich, G., de Mendoza, J., Prados, P.: Synthesis and photoisomerization of azocalixarenes with dendritic structures. Eur. J. Org. Chem. 2010, 1249–1257 (2010)
Kim, J.S., Lee, S.J., Jung, J.H., Hwang, I.C., Singh, N.J., Kim, S.K., Lee, S.H., Kim, H.J., Keum, C.S., Lee, J.W., Kim, K.S.: A color version of the Hinsberg test: 1 degrees–3 degrees amine indicator. Chem. Eur. J. 13, 3082–3088 (2007)
Thuéry, P., Nierlich, M., Lamare, É, Dozol, J.-F., Asfari, Z., Vicens, J.: Bis(crown ether) and azobenzocrown derivatives of calix[4]arene. A Review of structural information from crystallographic and modelling studies. J. Incl. Phenom. Macrocycl. Chem. 36, 375–408 (2000)
Hamada, F., Masuda, T., Kondo, Y.: Photoregulated-metal binding with an azobenzene-capped calix[4]arene. Supramol. Chem. 5, 129–131 (1995)
Yushkova, E.A., Zaikov, E.N., Stoikov, I.I., Antipin, I.S.: Self-assembly of nanosized aggregates based on the photoswitchable p-tert-butyl thiacalix[4]arene derivative and Fe(III), Cu(II), and Ag(I) cations. Russ. Chem. Bull. 58, 101–107 (2009)
Kim, J.S., Shon, O.J., Lee, J.K., Lee, S.H., Kim, J.Y., Park, K.-M., Lee, S.S.: Chromogenic azo-coupled calix[4]arenes. J. Org. Chem. 67, 1372–1375 (2002)
Saadioui, M., Asfari, Z., Thuéry, P., Nierlich, M., Vicens, J.: An azobenzene 1,3-alternate calix[4]-bis-crown and its 1:1 complex with cesium. Tetrahedron Lett. 38, 5643–5646 (1997)
Saadioui, M., Asfari, Z., Vicens, J.: Synthesis and characterisation of two azobenzene modified 1,3-calix[4]-bis-crowns as artificial potentially allosteric systems. Tetrahedron Lett. 38, 1187–1190 (1997)
Lee, S.H., Kim, J.Y., Ko, J., Lee, J.Y., Kim, J.S.: Regioselective complexation of metal ion in chromogenic calix[4]biscrowns. J. Org. Chem. 69, 2902–2905 (2004)
Park, J.M., Shon, O.J., Hong, H., Kim, J.S., Kim, Y., Lim, H.B.: Development of a microchip metal ion sensor using dinitro-azocalix[4]azacrown. Microchem. J. 80, 139–144 (2005)
Ashram, M.: Synthesis and extraction properties of new chromogenic azo-calix[4]dibenzothiacrown ethers. J. Incl. Phenom. Macrocycl. Chem. 59, 315–321 (2007)
Kamboh, M.A., Solangi, I.B., Sherazi, S.T., Memon, S.: Synthesis and application of calix[4]arene based resin for the removal of azo dyes. J. Hazard. Mater. 172, 234–239 (2009)
Bouoit-Montésinos, S., Bassus, J., Perrin, M., Lamartine, R.: Synthesis of new phenylazocalix[n]arenes (n = 4, 5). Tetrahedron Lett. 41, 2563–2567 (2000)
Karakus, O.O., Elcin, S., Yilmaz, M., Deligoz, H.: Removal of heavy metal ions from aqueous solution by azocalix[4]arene. Desalin. Water Treat. 26, 72–78 (2011)
Karakuş, ÖÖ, Deligöz, H.: Synthesis, extraction and chromogenic properties of amidoazocalix[4]arenes and their telomer derivatives. Supramol. Chem. 27, 110–122 (2014)
Tunç, M.M., Karakuş, ÖÖ, Deligöz, H.: Synthesis and characterization of azocalix[4]arene ester and ketone derivatives incorporated in a polymeric backbone with bisphenol-A and their cation-binding properties. J. Iran. Chem. Soc. 9, 729–735 (2012)
Tilki, T., Şener, İ., Karcı, F., Gülce, A., Deligöz, H.: An approach to the synthesis of chemically modified bisazocalix[4]arenes and their extraction properties. Tetrahedron 61, 9624–9629 (2005)
Wiktorowicz, S., Aseyev, V., Tenhu, H.: Novel photo-switchable polymers based on calix[4]arenes. Polym. Chem. 3, 1126–1129 (2012)
Wiktorowicz, S., Tenhu, H., Aseyev, V.: Influence of photo-isomerisation on host–guest interactions in poly(azocalix[4]arene)s. Polym. Chem. 4, 2898–2906 (2013)
Karakuş, ÖÖ, Deligöz, H.: Synthesis and characterization of tetrakis- derivatives of bisphenol-A with 4-phenylazoaniline and 5-(4-aminophenylazo)-25,26,27-tribenzoyloxy-28-hydroxycalix[4]arene. J. Appl. Polym. Sci. 122, 76–82 (2011)
Bonvallet, P.A., Mullen, M.R., Evans, P.J., Stoltz, K.L., Story, E.N.: Improved functionality and control in the isomerization of a calix[4]arene-capped azobenzene. Tetrahedron Lett. 52, 1117–1120 (2011)
Wiktorowicz, S., Tenhu, H., Aseyev, V.: Using light to tune thermo-responsive behavior and host–guest interactions in tegylated poly(azocalix[4]arene)s. Macromolecules 46, 6209–6216 (2013)
Elçin, S., Karakuş, ÖÖ, Kara, İ., Deligöz, H.: Synthesis and structural characterization of bisazocalix[4]arene with melamine: metal ion extraction studies. J. Mol. Liq. 202, 134–140 (2015)
Arora, V., Chawla, H.M., Francis, T., Nanda, M., Singh, S.P.: Synthesis of a new cesium selective calix[4]arene based chromoionophore. Indian J. Chem. Sect. A 42A, 3041–3043 (2003)
Chawla, H.M., Singh, S.P., Sahu, S.N., Upreti, S.: Shaping the cavity of calixarene architecture for molecular recognition: synthesis and conformational properties of new azocalix[4]arenes. Tetrahedron 62, 7854–7865 (2006)
van der Veen, N.J., Rozniecka, E., Woldering, L.A., Chudy, M., Huskens, J., van Veggel, F.C.J., M., Reinhoudt, D.N.: Highly selective optical-sensing membranes, containing calix[4]arene chromoionophores, for Pb2+ ions. Chem. Eur. J. 7, 4878–4886 (2001)
Chawla, H.M., Srinivas, K.: Synthesis of new chromogenic calix[4]arenes bridged at the upper rim through bisazobiphenyl linkages. J. Org. Chem. 61, 8464–8467 (1996)
Kim, J.Y., Kim, G., Kim, C.R., Lee, S.H., Lee, J.H., Kim, J.S.: UV band splitting of chromogenic azo-coupled calix[4]crown upon cation complexation. J. Org. Chem. 68, 1933–1937 (2003)
Yamamoto, H., Ueda, K., Sandanayake, K.R.A.S., Shinkai, S.: Molecular design of chromogenic calix[4]crowns which show very high Na+ selectivity. Chem. Lett. 24, 497–498 (1995)
Cho, E.J., Jeong, I.Y., Lee, S.J., Seo, J., Kim, H.J., Kim, E., Lee, S.S., Kang, J.K., Kim, J.S., Jung, J.H.: Discrimination of primary alkylamines using azobenzene-appended calix[4]arene derivatives in solution and in the solid state. Bull. Korean Chem. Soc. 28, 2519–2522 (2007)
Chawla, H.M., Singh, S.P., Upreti, S.: Synthesis of calix[4]arene(amido)monocrowns and their photoresponsive derivatives. Tetrahedron 62, 9758–9768 (2006)
Lee, S.H., Kim, S.K., Bok, J.H., Lee, S.H., Yoon, J., Lee, K., Kim, J.S.: Calix[4]crown in dual sensing functions with FRET. Tetrahedron Lett. 46, 8163–8167 (2005)
Chawla, H.M., Srinivas, K.: Molecular diagnostics: synthesis of new chromogenic calix[8]arenes as potential reagents for detection of amines. J. Chem. Soc. Chem. Commun. 22, 2593 (1994)
Mohindra Chawla, H., Srinivas, K.: Synthesis of new chromogenic calix(8)arenes. Tetrahedron Lett. 35, 2925–2928 (1994)
Choi, M.J., Kim, M.Y., Chang, S.-K.: A new Hg2+-selective chromoionophore based on calix[4]arenediazacrown ether. Chem. Commun. 17, 1664–1665 (2001)
Chen, C.-F., Chen, Q.-Y.: Azocalix[4]arene-based chromogenic anion probes. New J. Chem. 30, 143–147 (2006)
Thiampanya, P., Muangsin, N., Pulpoka, B.: Azocalix[4]arene strapped calix[4]pyrrole: a confirmable fluoride sensor. Org. Lett. 14, 4050–4053 (2012)
Gordon, J.L.M., Böhmer, V., Vogt, W.: A calixarene-based chromoionophore for the larger alkali metals. Tetrahedron Lett. 36, 2445–2448 (1995)
Arduini, A., Pochini, A., Secchi, A.: Rigid calix[4]arene as a building block for the synthesis of new quaternary ammonium cation receptors. Eur. J. Org. Chem. 2000, 2325–2334 (2000)
Dong, Y.-Y., Kim, T.-H., Lee, C.-S., Kim, H.-J., Lee, J.-H., Lee, J.-H., Kim, H.-S., Kim, J.-S.: Voltammetric studies of diazocalix[4]crown-6 for metal ion sensing. Bull. Korean Chem. Soc. 31, 3549–3552 (2010)
Jin, C.-M., Lu, G.-Y., Wang, Z.-S., You, X.-Z., Wang, Z.-H., Gong, W., Wu, H.-M.: Synthesis of heteroarylazo-substituted calix[4]arenes. Synthesis 2001, 1023–1026 (2001)
Deligöz, H.: Synthesis and properties of a series of novel calix[6]arene diazo derivatives. J. Incl. Phenom. Macrocycl. Chem. 43, 285–289 (2002)
Chawla, H.M., Venkatesan, N., Kumar, S.: Synthesis of new chromogenic calix[4]arene based molecular receptors for palladium and platinum. J. Incl. Phenom. Macrocycl. Chem. 74, 239–249 (2012)
Şener, İ., Şener, N., Erişkin, S.: Synthesis and absorption spectra of some novel hetaryltetrakisazocalix[4]arene derivatives. Dyes Pigm. 96, 256–263 (2013)
Akdoğan, A., Deniz, M., Cebecioğlu, S., Şen, A., Deligöz, H.: Liquid–liquid extraction of transition metal cations by nine new azo derivatives calix[n]arene. Sep. Sci. Technol. 37, 973–980 (2002)
Lu, J., Tong, X., He, X.: A mercury ion-selective electrode based on a calixarene derivative containing the thiazole azo group. J. Electroanal. Chem. 540, 111–117 (2003)
Ak, M.S., Deligöz, H.: The synthesis of ester and ketone derivatives of azocalix[4]arene containing chromogenic groups. J. Incl. Phenom. Macrocycl. Chem. 55, 223–228 (2006)
Ak, M., Taban, D., Deligoz, H.: Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes. J. Hazard. Mater. 154, 51–54 (2008)
Sener, I., Karci, F., Kilic, E., Deligoz, H.: Azocalixarenes. 3: synthesis and investigation of the absorption spectra of hetarylazo disperse dyes derived from calix[4]arene. Dyes Pigm. 62, 141–148 (2004)
Rouis, A., Dridi, C., Ben Chaabane, R., Davenas, J., Aeiyach, S., Ben Ouada, H., Dumazet-Bonnamour, I., Halouani, H.: Optical and electrical study of chromogenic calix[4]arene derivatives. Mater. Sci. Eng. C 26, 240–246 (2006)
Rouis, A., Mlika, R., Dridi, C., Davenas, J., Ben Ouada, H., Halouani, H., Bonnamour, I., Jaffrezic, N.: Optical spectroscopy studies of the complexation of chromogenic azo-calix[4]arene with Eu3+, Ag+ and Cu2+ ions. Mater. Sci. Eng. C 26, 247–252 (2006)
Şener, I., Karci, F., Kiliç, E., Deligöz, H.: Azocalixarenes. 4: synthesis, characterization and investigation of the absorption spectra of hetarylazo-substituted calix[6]arenes. Dyes Pigm. 62, 149–157 (2004)
Kao, T.L., Wang, C.C., Pan, Y.T., Shiao, Y.J., Yen, J.Y., Shu, C.M., Lee, G.H., Peng, S.M., Chung, W.S.: Upper rim allyl- and arylazo-coupled calix[4]arenes as highly sensitive chromogenic sensors for Hg2+ ion. J. Org. Chem. 70, 2912–2920 (2005)
Chakrabarti, A., Chawla, H.M., Francis, T., Pant, N., Upreti, S.: Synthesis and cation binding properties of new arylazo- and heteroarylazotetrathiacalix[4]arenes. Tetrahedron 62, 1150–1157 (2006)
Fan, P., Wan, L., Shang, Y., Wang, J., Liu, Y., Sun, X., Chen, C.: Spectroscopic investigation of the interaction of water-soluble azocalix[4]arenes with bovine serum albumin. Bioorg. Chem. 58, 88–95 (2015)
Arroyave, F.A., Ballester, P.: Reversible light-controlled cargo release in hydrogen-bonded dimeric capsules. J. Org. Chem. 80, 10866–10873 (2015)
Diaz-Moscoso, A., Arroyave, F.A., Ballester, P.: Moving systems of polar dimeric capsules out of thermal equilibrium by light irradiation. Chem. Commun. 52, 3046–3049 (2016)
Shinkai, S., Araki, K., Shibata, J., Tsugawa, D., Manabe, O.: Autoaccelerative diazo coupling with calix[4]arene: substituent effects on the unusual co-operativity of the OH groups. J. Chem. Soc. Perkin Trans. 1 12, 3333 (1990)
Bingol, H., Kocabas, E., Zor, E., Coskun, A.: A novel benzothiazole based azocalix[4]arene as a highly selective chromogenic chemosensor for Hg2+ ion: a rapid test application in aqueous environment. Talanta 82, 1538–1542 (2010)
Karcı, F., Sener, I., Deligoz, H.: Azocalixarenes. 1: synthesis, characterization and investigation of the absorption spectra of substituted azocalix[4]arenes. Dyes Pigm. 59, 53–61 (2003)
Ehlinger, N., Lecocq, S., Perrin, R., Perrin, M.: Study of calixarenes-dyes. Structure of p-tetrakis(phenylazo)calix[4]arene. Supramol. Chem. 2, 77–82 (1993)
Chawla, H.M., Singh, S.P., Upreti, S.: Synthesis of cesium selective pyridyl azocalix[n]arenes. Tetrahedron 62, 2901–2911 (2006)
Oueslati, F., Dumazet-Bonnamour, I., Lamartine, R.: Synthesis of new chromogenic 2,2′-bithiazoylcalix[4]arenes. Tetrahedron Lett. 42, 8177–8180 (2001)
Tóth, K., Thu Lan, B.T., Jeney, J., Horváth, M., Bitter, I., Grün, A., Ágai, B., Tódke, L.: Chromogenic calix[4]arene as ionophore for potentiometric and optical sensors. Talanta 41, 1041–1049 (1994)
Hisada, K., Tanaka, K., Hori, T., Sakon, H., Tokunaga, Y.: Preparation of supramolecular assembled films of fullerene C60 on the aqueous solution of water-soluble azocalixarene. Compos. Interfaces 11, 315–324 (2004)
Liu, C.J., Lin, J.T., Wang, S.H., Jiang, J.C., Lin, L.G.: Chromogenic calixarene sensors for amine detection. Sens. Actuator B 108, 521–527 (2005)
Tokunaga, Y., Sakon, H., Kanefusa, H., Shimomura, Y., Suzuki, K.: Molecular dynamics of amphiphilic calixarene. Arkivoc 8, 135–143 (2003)
Karakuş, ÖÖ, Deligöz, H.: Ester and ketone groups substituted mono- and di-azo-coupled azocalix[4]arenes as extractant for Hg+ and Hg2+, or Cr3+ cations. J. Macromol. Sci. A 47, 1111–1115 (2010)
Ak, M.S., Deligöz, H.: Azocalixarenes. 6: synthesis, complexation, extraction and thermal behaviour of four new azocalix[4]arenes. J. Incl. Phenom. Macrocycl. Chem. 59, 115–123 (2007)
Karcı, F., Şener, İ., Deligöz, H.: Azocalixarenes. 2: synthesis, characterization and investigation of the absorption spectra of azocalix[6]arenes containing chromogenic groups. Dyes Pigm. 62, 131–140 (2004)
Ma, H., Jarzak, U., Thiemann, W.: Synthesis and spectroscopic properties of new luminol-linked calixarene derivatives. Anal. Chim. Acta 362, 121–129 (1998)
Oueslati, F., Dumazet-Bonnamour, I., Lamartine, R.: New azothiacalix[4]arenes containing biheterocyclic subunits: extraction and complexation properties. Supramol. Chem. 17, 227–232 (2005)
Shinkai, S., Araki, K., Shibata, J., Manabe, O.: Autoaccelerative diazo coupling with calix[4]arene: unusual co-operativity of the calixarene hydroxy groups. J. Chem. Soc. Perkin Trans. 1 1, 195 (1989)
Shinkai, S., Araki, K., Shibata, J., Tsugawa, D., Manabe, O.: Diazo-coupling reactions with calix[4]arene. pKa determination with chromophoric azocalix[4]arenes. Chem. Lett. 18, 931–934 (1989)
Ehlinger, N., Perrin, M.: Structure of p-tetrakis-(4-nitrophenylazo)calix[4]-arene-4-picoline (1:4) complex. J. Incl. Phenom. Mol. Recognit. Chem. 22, 33–40 (1995)
Jin, C.-M., Wang, Z., Zhang, K.-L., Lu, G.-Y., You, X.-Z.: Crystal structure of the molecular adduct of 5-mono[(4-nitrophenyl)azo]-25,26,27,28-tetrahydroxycalix[4]arene with chloroform (1:1). J. Chem. Crystallogr. 32, 293–297 (2002)
Guo, X., Zhang, L., Lu, G.-y., Zhang, C.-z., Jin, C.-m., Liu, M.-h.: p-Nitrophenylazo calix[4]arenes, synthesis, monolayers and NLO-properties. Supramol. Chem. 17, 271–276 (2005)
Jin, C.-M., Gui, M.-Z., Lu, G.-Y., Guo, X., Zhang, H., You, X.-Z.: Studies on properties of p-nitrophenylazo calix[4]arene derivatives. Chin. J. Chem. 21, 105–107 (2010)
Jin, C.-M., Lu, G.-Y., Liu, Y., You, X.-Z., Wang, Z.-H., Wu, H.-M.: Synthesis of (p-substituted phenyl)azo calix[4]arenes. Chin. J. Chem. 20, 1080–1087 (2010)
Gu, J.W., Tang, J., Sun, Y., Li, L., Xu, Z., Lv, Z., Chen, X.L., Liu, E.H.: Research on synthesis of new azo calix[4]arene and its dyeing properties. In: MATEC Web of Conferences, vol. 25, pp. 02016 (2015)
Morita, Y., Agawa, T., Kai, Y., Kanehisa, N., Kasai, N., Nomura, E., Taniguchi, H.: Syntheses and crystal structure of calix[4]quinone. Chem. Lett. 18, 1349–1352 (1989)
Morita, Y., Agawa, T., Nomura, E., Taniguchi, H.: Syntheses and NMR behavior of calix[4]quinone and calix[4]hydroquinone. J. Org. Chem. 57, 3658–3662 (1992)
Tyson, J.C., Collard, D.M., Hughes, K.D.: Chromophoric water-soluble tetrakis(4-carboxyphenylazo)-calix[4]arene: binding of arylammonium ions and benzene. J. Incl. Phenom. Mol. Recognit. Chem. 29, 109–118 (1997)
Lu, J., Chen, R., He, X.: A lead ion-selective electrode based on a calixarene carboxyphenyl azo derivative. J. Electroanal. Chem. 528, 33–38 (2002)
Lu, L., Zhu, S., Liu, X., Xie, Z., Yan, X.: Highly selective chromogenic ionophores for the recognition of chromium(III) based on a water-soluble azocalixarene derivative. Anal. Chim. Acta 535, 183–187 (2005)
Zhou, Y., Xu, H., Yu, H., Chun, L., Lu, Q., Wang, L.: Spectrofluorometric study on the inclusion behavior of p-(p-carboxyl benzeneazo) calix[4]arene with norfloxacin. Spectrochim. Acta A 70, 411–415 (2008)
Liu, L., Ren, Z., Li, H., Shang, H., Lang, J.: 5,11,17,23-Tetrakis[(p-carboxyphenyl)azo]-25,26,27,28-tetrahydroxy calix[4]arene: crystal structure and pH sensing properties. Chin. J. Chem. 28, 1829–1834 (2010)
Patel, R.V., Panchal, J.G., Rana, V.A., Menon, S.K.: Liquid crystals based on calix[4]arene Schiff bases. J. Incl. Phenom. Macrocycl. Chem. 66, 285–295 (2010)
Uygun, A., Yavuz, A.G., Sen, S., Deligoz, F., Karakus, O.O., Deligoz, H.: Characterization of polypyrrole/azocalix[4]arene salts: electrical properties and thermal stability. J. Appl. Polym. Sci. 115, 2697–2702 (2010)
Elçin, S., İlhan, M.M., Deligöz, H.: Synthesis and spectral characterization of azo dyes derived from calix[4]arene and their application in dyeing of fibers. J. Incl. Phenom. Macrocycl. Chem. 77, 259–267 (2013)
Kim, T.H., Kim, J.S., Kim, H.: Spectrophotometric and electrochemical study of Cu2+-selective azocalix[4]arene bearing p-carboxyl group. Bull. Korean Chem. Soc. 34, 3377–3380 (2013)
Bouoit-Montésinos, S., Vocanson, F., Bassus, J., Lamartine, R.: Synthesis of new calix[9]arenes. Synth. Commun. 30, 911–915 (2000)
Oueslati, F., Dumazet-Bonnamour, I., Lamartine, R.: Synthesis and extraction properties of multifunctionalized azocalix[4]arenes containing bipyridyl subunits. New J. Chem. 28, 1575–1578 (2004)
Deligoz, H., Erdem, E.: Liquid–liquid extraction of transition metal cations by diazo coupling calix[4]arene derivatives. Solvent Extr. Ion Exch. 15, 811–817 (1997)
Xing, Y.-J., Wang, Y.-J.: Synthesis and conformation of new azo-functionalized calix[4]arenes. Chin. J. Chem. 24, 1209–1213 (2006)
Mlika, R., Rouis, A., Bonnamour, I., Ouada, H.B.: Impedance spectroscopic investigation of the effect of thin azo-calix[4]arene film type on the cation sensitivity of the gold electrodes. Mater. Sci. Eng. C 31, 1466–1471 (2011)
Halouani, H., Dumazet-Bonnamour, I., Lamartine, R.: Synthesis of novel chromogenic bi- and tri-functionalized calix[4]arenes. Tetrahedron Lett. 43, 3785–3788 (2002)
Rouis, A., Dridi, C., Dumazet-Bonnamour, I., Davenas, J.,, Ben Ouada, H.: Transport mechanism and trap distribution in ITO/azo-calix[4]arene derivative/Al diode structure. Physica B 399, 109–115 (2007)
Dridi, C., Ben Chaabane, R., Davenas, J., Bonnamour-Dumazet, I., Ben Ouada, H.: Nanostructural, optical and electrical properties of vacuum evaporated films of an azo-calix[4]arene derivative. Vacuum 83, 883–888 (2009)
Karakuş, ÖÖ, Deligöz, H.: Synthesis and characterization of three novel azocalix[4]arene Schiff base derivatives and their selective copper extraction. J. Iran. Chem. Soc. 9, 93–100 (2012)
Tyson, J.C., Moore, J.L., Hughes, K.D., Collard, D.M.: Amphiphilic cup-shaped [(4-alkylphenyl)azo]-substituted calixarenes: self-assembly and host–guest chemistry at the air–water interface. Langmuir 13, 2068–2073 (1997)
Desroches, C., Parola, S., Vocanson, F., Ehlinger, N., Miele, P., Lamartine, R., Bouix, J., Eriksson, A., Lindgren, M., Lopes, C.: Synthesis, characterization and optical power limiting behaviour of phenylazo- and 4-nitrophenylazo-tetrahydroxytetrathiacalix[4]arene. J. Mater. Chem. 11, 3014–3017 (2001)
Perrin, M., Bavoux, C., Vocanson, F., Lamartine, R., Desroches, C., Miele, P., Parola, S.: The structure of the pyridine complex of p-tetrakis(phenylazo)-tetra-hydroxythiacalix[4]arene. J. Incl. Phenom. Macrocycl. Chem. 46, 15–17 (2003)
Özkınalı, S.: Spectroscopic and thermal properties of newly mixed azocalix[4]arene ester derivatives. Dyes Pigm. 107, 81–89 (2014)
Nomura, E., Taniguchi, H., Tamura, S.: Selective ion extraction by a calix[6]arene derivative containing azo groups. Chem. Lett. 18, 1125–1126 (1989)
Ma, Q., Ma, H., Su, M., Wang, Z., Nie, L., Liang, S.: Determination of nickel by a new chromogenic azocalix[4]arene. Anal. Chim. Acta 439, 73–79 (2001)
Ma, Q., Ma, H., Wang, Z., Su, M., Xiao, H., Liang, S.: A highly selective calix[4]arene-based chromoionophore for Ni2+. Chem. Lett. 30, 100–101 (2001)
Halouani, H., Dumazet-Bonnamour, I., Duchamp, C., Bavoux, C., Ehlinger, N., Perrin, M., Lamartine, R.: Synthesis, conformations and extraction properties of new chromogenic calix[4]arene amide derivatives. Eur. J. Org. Chem. 2002, 4202–4210 (2002)
Benounis, M., Jaffrezic-Renault, N., Halouani, H., Lamartine, R., Dumazet-Bonnamour, I.: Detection of heavy metals by an optical fiber sensor with a sensitive cladding including a new chromogenic calix[4]arene molecule. Mater. Sci. Eng. C 26, 364–368 (2006)
Lhoták, P., Morávek, J., Stibor, I.: Diazo coupling: an alternative method for the upper rim amination of thiacalix[4]arenes. Tetrahedron Lett. 43, 3665–3668 (2002)
Dong, Y., Kim, T.H., Kim, H.J., Lee, M.H., Lee, S.Y., Mahajan, R.K., Kim, H., Kim, J.S.: Spectroscopic and electrochemical studies of two distal diethyl ester azocalix[4]arene derivatives. J. Electroanal. Chem. 628, 119–124 (2009)
Ramanjaneyulu, P.S., Singh, P., Sayi, Y.S., Chawla, H.M., Ramakumar, K.L.: Ion selective electrode for cesium based on 5-(4′-nitrophenylazo)25,27-bis(2-propyloxy)26,28-dihydroxycalix[4]arene. J. Hazard. Mater. 175, 1031–1036 (2010)
Senthil, K., Akiba, U., Fujiwara, K., Hamada, F., Kondo, Y.: High selectivity and extractability of palladium from chloride leach liquors of an automotive catalyst residue by azothiacalix[4]arene derivative. Hydrometallurgy 169, 478–487 (2017)
Oueslati, F., Dumazet-Bonnamour, I., Lamartine, R.: New chromogenic azocalix[4]arene podands incorporating 2,2′-bipyridyl subunits Electronic supplementary information (ESI) available: mole ratio plot for mixtures of 4a and Zn(CF3SO3)2; UV-Vis spectra for 4a (5 × 10−6 mol l−1) when Zn2+ (5 × 10−5 mol l−1) is added to the CH2Cl2 host solution. New J. Chem. 27, 644–647 (2003). http://www.rsc.org/suppdata/nj/b2/b209528a
Wang, N.-J., Sun, C.-M., Chung, W.-S.: A specific and ratiometric chemosensor for Hg2+ based on triazole coupled ortho-methoxyphenylazocalix[4]arene. Tetrahedron 67, 8131–8139 (2011)
Menon, S.K., Patel, R.V., Panchal, J.G.: The synthesis and characterization of calix[4]arene based azo dyes. J. Incl. Phenom. Macrocycl. Chem. 67, 73–79 (2010)
Shu, C.-m., Yuan, T.-s., Ku, M.-c., Ho, Z.-c., Liu, W.-c., Tang, F.-s., Lin, L.-g.: Diallylbis(arylazo)calix[4]arenes: the syntheses of calix[4]arenes with two different para-substituents. Tetrahedron 52, 9805–9818 (1996)
Lang, K., Prošková, P., Kroupa, J., Morávek, J., Stibor, I., Pojarová, M., Lhoták, P.: The synthesis and complexation of novel azosubstituted calix[4]arenes and thiacalix[4]arenes. Dyes Pigm. 77, 646–652 (2008)
Deligoz, H., Erdem, E., Kocaokutgen, H.: Solvent extraction of Fe3+ cation by diazo-coupling calix [4] arenes. Turk. J. Chem. 24, 157–164 (2000)
Deligoz, H., Ozen, O., Cilgi, G.K., Cetisli, H.: A study on the thermal behaviours of parent calix[4]arenes and some azocalix[4]arene derivatives. Thermochim. Acta 426, 33–38 (2005)
Deligöz, H., Ercan, N.: The synthesis of some new derivatives of calix[4]arene containing azo groups. Tetrahedron 58, 2881–2884 (2002)
Bayrakdar, A., Kart, H.H., Elcin, S., Deligoz, H., Karabacak, M.: Synthesis and DFT calculation of a novel 5,17-di(2-antracenylazo)-25,27-di(ethoxycarbonylmethoxy)-26,28-dihydroxycalix[4]a rene. Spectrochim. Acta A 136(Pt B), 607–617 (2015)
Elçin, S., Deligöz, H., Bhatti, A.A., Oguz, M., Karakurt, S., Yilmaz, M.: Synthesis and evaluation of fluorescence properties of Cu2+ selective azocalix[4]arenes and their application in living cell imaging. Sens. Actuators B 234, 345–352 (2016)
Deligöz, H., Çetisli, H.: The synthesis and properties of some novel azo group containing calix[n]arene derivatives. J. Chem. Res. 2001, 427–429 (2001)
Yeh, M.-l., Tang, F.-s., Chen, S.-l., Liu, W.-c., Lin, L.-g.: Syntheses of 6-amino-1,3-benzodioxin and its p-arylazo-substituted calix[4]arenes. J. Org. Chem. 59, 754–757 (1994)
Karakuş, ÖÖ, Çilgi, G.K., Deligöz, H.: Thermal analysis of two series mono- and di-azocalix[4]arene derivatives. J. Therm. Anal. Calorim. 105, 341–347 (2011)
Karakuş, ÖÖ, Deligöz, H.: Azocalixarenes.8: synthesis and investigation of the absorption spectra of di-substituted azocalix[4]arenes containing chromogenic groups. J. Incl. Phenom. Macrocycl. Chem. 61, 289–296 (2008)
Karakuş, ÖÖ, Deligöz, H.: Efficient and selective extraction of Fe3+ by mono- and di-azocalix[4]arene derivatives. Anal. Lett. 43, 768–775 (2010)
Chang, K.-C., Su, I.-H., Lee, G.-H., Chung, W.-S.: Triazole- and azo-coupled calix[4]arene as a highly sensitive chromogenic sensor for Ca2+ and Pb2+ ions. Tetrahedron Lett. 48, 7274–7278 (2007)
Chang, K.-C., Su, I.-H., Wang, Y.-Y., Chung, W.-S.: A bifunctional chromogenic calix[4]arene chemosensor for both cations and anions: a potential Ca2+ and F- switched INHIBIT logic gate with a YES logic function. Eur. J. Org. Chem. 2010, 4700–4704 (2010)
Chen, Y.-J., Chung, W.-S.: Tetrazoles and para-substituted phenylazo-coupled calix[4]arenes as highly sensitive chromogenic sensors for Ca2+. Eur. J. Org. Chem. 2009, 4770–4776 (2009)
Ho, I.T., Lee, G.H., Chung, W.S.: Synthesis of upper-rim allyl- and p-methoxyphenylazocalix[4]arenes and their efficiencies in chromogenic sensing of Hg2+ ion. J. Org. Chem. 72, 2434–2442 (2007)
Elcin, S., Cilgi, G.K., Karakus, O.O., Deligoz, H.: A study on thermal behaviors of mono ethyl ester azocalix[4]arene derivatives. J. Therm. Anal. Calorim. 118, 719–722 (2014)
Elçin, S., Deligöz, H.: Internal charge transfer based Hg-sensing azocalix[4]arene mono anthracenate derivatives. Sens. Actuator B 211, 83–92 (2015)
Echabaane, M., Rouis, A., Bonnamour, I., Ouada, H.B.: Characterization of an azo-calix[4]arene-based optical sensor for europium(III) ions. Mater. Sci. Eng. C 32, 1218–1221 (2012)
Rouis, A., Davenas, J., Bonnamour, I., Ben Ouada, H.: Studies of morphological optical and electrical properties of the MEH-PPV/azo-calix[4]arene composite layers. Physica B 474, 70–76 (2015)
Rouis, A., Mlika, R., Davenas, J., Ben Ouada, H., Bonnamour, I., Jaffrezic, N.: Impedance spectroscopic investigations of ITO modified by new Azo-calix[4]arene immobilised into electroconducting polymer (MEHPPV). J. Electroanal. Chem. 601, 29–38 (2007)
Usta, K., Karakus, O., Usta, O., Deligoz, A.: H.: Identification of radiation-induced radical structure in azocalix[4]arene: an EPR study. Magn. Reson. Chem. 51, 671–675 (2013)
Elcin, S., Cilgi, G.K., Bayrakdar, A., Deligoz, H.: The synthesis and characterization of azocalix[4]arene based chemosensors and investigation of their properties. Spectrochim. Acta A 142, 178–187 (2015)
Bingol, H., Kocabas, E., Zor, E., Coskun, A.: Spectrophotometric and electrochemical behavior of a novel azocalix[4]arene derivative as a highly selective chromogenic chemosensor for Cr3+. Electrochim. Acta 56, 2057–2061 (2011)
Bal, Z., Yu, L., Lu, G.-Y., Guo, X.: Synthesis of (p-formylphenyl)azo calix[4]arenes. Chin. J. Chem. 22, 498–501 (2010)
Şener, İ., Kadifeli, F.: Synthesis and absorption spectra of some novel hetaryldisazocalix[4]arene derivatives. Color. Technol. 127, 404–410 (2011)
Tayeb, R., Zaghbani, A., Maamar, S.B., Meganem, F., Vocanson, F., Dhahbi, M.: Evaluation of an azocalix[4]arene derivative for the selective extraction of Pd(II) from hydrochloric acid solutions. C. R. Chim. 12, 1275–1279 (2009)
Echabaane, M., Rouis, A., Bonnamour, I., Ben Ouada, H.: Studies of aluminum(III) ion-selective optical sensor based on a chromogenic calix[4]arene derivative. Spectrochim. Acta A 115, 269–274 (2013)
Elçin, S., Çılgı, G.K., Deligöz, H.: Thermal behaviors of bisazocalix[4]arene derivatives. Polycycl. Aromat. Compd. 37, 46–51 (2017)
Elçin, S., Deligöz, H.: Di-substituted azocalix[4]arenes containing chromogenic groups: synthesis, characterization, extraction, and thermal behavior. Tetrahedron 69, 6832–6838 (2013)
Elçin, S., Deligöz, H.: Synthesis and metal extraction studies of a novel chromogenic 5,17-bisazocalix[4]arenes. J. Incl. Phenom. Macrocycl. Chem. 80, 337–343 (2014)
Kart, H.H., Bayrakdar, A., Elcin, S., Deligoz, H., Karabacak, M.: Synthesis and investigation of the properties of novel azocalix[4]arenes. Spectrochim. Acta A 146, 151–162 (2015)
Kim, T.H.: Spectrophotometric and electrochemical study for metal ion binding of azocalix[4]arene bearing p-ethylester group. Spectrochim. Acta A 178, 8–13 (2017)
Korkmaz Alpoguz, H., Kaya, A., Deligöz, H.: Liquid membrane transport of Hg(II) by an azocalix[4]arene derivative. Sep. Sci. Technol. 41, 1155–1167 (2006)
Zor, E., Saf, A.O., Bingol, H.: Spectrophotometric and voltammetric characterization of a novel selective electroactive chemosensor for Mg2+. Cent. Eur. J. Chem. 11, 554–560 (2013)
Agrawal, Y.K., Desai, N.C., Mehta, N.D.: Microwave-assisted synthesis of azocalixarenes. Synth. Commun. 37, 2243–2252 (2007)
Ebdelli, R., Rouis, A., Mlika, R., Bonnamour, I., Ouada, B., Davenas, H.: J.: Photo-physical and complexation properties of chromogenic azo-calix[4]arene: application to the detection of Eu3+. J. Mol. Struct. 1006, 210–215 (2011)
Ebdelli, R., Ben Dkhil, S., Azib, T., Ben Chaabane, R., Dumazet-Bonnamour, I., Ben Ouada, H., Davenas, J.: Electrical, optical and morphological properties of a new chromogenic calix[4]arene derivative. Synth. Met. 197, 112–118 (2014)
Elçin, S., Deligöz, H.: A versatile approach toward chemosensor for Hg2+ based on para-substituted phenylazocalix[4]arene containing mono ethyl ester unit. Dyes Pigm. 107, 166–173 (2014)
Su, P.-G., Lin, L.-G., Lin, P.-H.: Detection of Cu(II) ion by an electrochemical sensor made of 5,17-bis(4′-nitrophenylazo)-25,26,27,28-tetrahydroxycalix[4]arene-electromodified electrode. Sens. Actuator B 191, 364–370 (2014)
Chawla, H.M., Sahu, S.N.: Synthesis of novel chromogenic azocalix[4]arenemonoquinones and their binding with alkali metal cations. J. Incl. Phenom. Macrocycl. Chem. 63, 141–149 (2009)
van der Veen, N.J., Egberink, R.J.M., Engbersen, J.F.J., van Veggel, F.J.C.M., Reinhoudt, D.N.: Conformationally flexible calix[4]arene chromoionophores: optical transduction of soft metal ion complexation by cation–π interactions. Chem. Commun. 8, 681–682 (1999)
Kim, N.Y., Chang, S.-K.: Calix[4]arenes bearing two distal azophenol moieties: highly selective chromogenic ionophores for the recognition of Ca2+ ion. J. Org. Chem. 63, 2362–2364 (1998)
Van Tan, L., Quang, D.T., Lee, M.H., Kim, T.H., Kim, H., Kim, J.S.: Tetradiazo(o-carboxy)phenylcalix[4]arene for determination of Pb2+ ion. Bull. Korean Chem. Soc. 28, 791–794 (2007)
Kim, T.H., Kim, S.H., Tan, L.V., Seo, Y.J., Park, S.Y., Kim, H., Kim, J.S.: Transition metal ion selective ortho-ester diazophenylcalix[4]arene. Talanta 71, 1294–1297 (2007)
Kim, T.H., Kim, S.H., Tan, L.V., Dong, Y., Kim, H., Kim, J.S.: Diazo-coupled calix[4]arenes for qualitative analytical screening of metal ions. Talanta 74, 1654–1658 (2008)
Hieu, T.Q., Tuan, N.N., Tu, L.N., Tan, L.V.: Structural study on the complex of ortho-ester tetra azophenylcalix[4]arene (TEAC) with Th(IV). Int. J. Chem. 3, 97–104 (2011)
Kim, B., Kim, T.H.: Electrochemical studies for cation recognition with diazo-coupled calix[4]arenes. J. Anal. Methods Chem. 2015, 579463 (2015)
Tan, V.L., Hieu, Q.T., Cuong, V.N.: Spectrophotometric determination of Cr(III) and Pb(II) using their complexes with 5,11,17,23-tetra[(2-ethyl acetoethoxyphenyl)(azo)phenyl]calix[4]arene. J. Anal. Methods Chem. 2015, 860649 (2015)
Tran, Q.H., Le, V.T., Nguyen, V.C.: Solvent extraction of thorium using 5,11,17,23-tetra[(2-ethyl acetoethoxyphenyl)(azo)phenyl]calix[4]arene. J. Chem. 2016, 5078462 (2016)
Jain, V.K., Kanaiya, P.H.: Chemistry of calix[4]resorcinarenes. Russ. Chem. Rev. 80, 75–102 (2011)
Timmerman, P., Verboom, W., Reinhoudt, D.N.: Resorcinarenes. Tetrahedron 52, 2663–2704 (1996)
Şener, İ., Şarkaya, K.: Synthesis and investigation absorption features of some novel hetarylazo dyes derived from calix[4]resorcinarene. SDU J. Sci. 8, 175–189 (2013)
Jain, V.K., Pillai, S.G., Kanaiya, P.H.: Synthesis of calix[4]resorcinarene based dyes and its application in dyeing of fibres. E-J. Chem. 5, 1037–1047 (2008)
Husaru, L., Gruner, M., Wolff, T., Habicher, W.D., Salzer, R.: Photoresponsive upper-rim azobenzene substituted calix[4]resorcinarenes. Tetrahedron Lett. 46, 3377–3379 (2005)
Ichimura, K., Fukushima, N., Fujimaki, M., Kawahara, S., Matsuzawa, Y., Hayashi, Y., Kudo, K.: Macrocyclic amphiphiles. 1. Properties of calix[4]resorcinarene derivatives substituted with azobenzenes in solutions and monolayers. Langmuir 13, 6780–6786 (1997)
Ichimura, K.: Light-driven motion of liquids on a photoresponsive surface. Science 288, 1624–1626 (2000)
Jain, V.K., Kanaiya, P.H.: Diazo reductive: a new approach to the synthesis of novel “upper rim” functionalized resorcin[4]arene Schiff-bases. J. Incl. Phenom. Macrocycl. Chem. 62, 111–115 (2008)
Sakano, T., Ohashi, T., Yamanaka, M., Kobayashi, K.: Photoresponsive self-assembled hexameric capsules based on calix[4]resorcinarenes bearing azobenzene dendron conjugates as side chains. Org. Biomol. Chem. 13, 8359–8364 (2015)
Jain, V., Kanaiya, P., Bhojak, N.: Synthesis, spectral characterization of azo dyes derived from calix[4]resorcinarene and their application in dyeing of fibers. Fibers Polym. 9, 720–726 (2008)
Anjali, B., Chawla, H.M.: Synthesis and applications of chromogenic calix [4] resorcinarene derivatives. Res. J. Chem. Environ. 18, 45–59 (2014)
Ueda, M., Fukushima, N., Kudo, K., Ichimura, K.: Photocontrolled dispersibility of colloidal silica by surface adsorption of a calix[4]resorcinarene having azobenzene groups. J. Mater. Chem. 7, 641–645 (1997)
Fujimaki, M., Kawahara, S., Matsuzawa, Y., Kurita, E., Hayashi, Y., Ichimura, K.: Macrocyclic amphiphiles. 3. Monolayers of O-octacarboxymethoxylated calix[4]resorcinarenes with azobenzene residues exhibiting efficient photoisomerizability. Langmuir 14, 4495–4502 (1998)
Fujimaki, M., Matsuzawa, Y., Hayashi, Y., Ichimura, K.: Monolayers of calix[4]resorcinarenes with azobenzene residues exhibiting efficient photoisomerizability. Chem. Lett. 27, 165–166 (1998)
Ichimura, K., Fujimaki, M., Matsuzawa, Y., Hayashi, Y., Nakagawa, M.: Characteristics of monolayers of calix[4]resorcinarenes derivatives having azobenzene chromophores. Mater. Sci. Eng. C 8–9, 353–359 (1999)
Berryman, O.B., Sather, A.C., Lledo, A., Rebek, J.: Switchable catalysis with a light-responsive cavitand. Angew. Chem. Int. Ed. 50, 9400–9403 (2011)
Berryman, O.B., Sather, A.C., Rebek, J.: A light controlled cavitand wall regulates guest binding. Chem. Commun. 47, 656–658 (2011)
Poleska-Muchlado, Z., Luboch, E., Biernat, J.F.: Novel calix[4]resorcinarenes with side azobenzo-15-crown-5 residues. Synth. Commun. 38, 3062–3067 (2008)
Manabe, O., Asakura, K., Nishi, T., Shinkai, S.: Diazo-coupling with a resorcinol-based cyclophane. A new water-soluble host with a deep cleft. Chem. Lett. 19, 1219–1222 (1990)
Sahu, S.N., Rozhenko, A.B., Eberhard, J., Mattay, J.: Synthesis of a new photoresponsive molecular carcerand. J. Photochem. Photobiol. A 331, 165–174 (2016)
Omar, O., Ray, A.K., Hassan, A.K., Davis, F.: Resorcinol calixarenes (resorcarenes): Langmuir–Blodgett films and optical properties. Supramol. Sci. 4, 417–421 (1997)
Hassan, A.K., Nabok, A.V., Ray, A.K., Davis, F., Stirling, C.J.M.: Complexation of metal ions with Langmuir–Blodgett films of novel calixarene azo-derivative. Thin Solid Films 327–329, 686–689 (1998)
Hassan, A.K., Ray, A.K., Nabok, A.V., Davis, F.: Spun films of novel calix[4]resorcinarene derivatives for benzene vapour sensing. Sens. Actuator B 77, 638–641 (2001)
Hassan, A.K., Goy, C., Nabok, A.V.: Interaction of volatile organic vapours with azo-calix[4]-resorcinarene and poly(9-vinylcarbazole) thin films using SPR measurements. Thin Solid Films 516, 9006–9011 (2008)
Busseron, E., Lux, J., Degardin, M., Rebek, J.: Synthesis and recognition studies with a ditopic, photoswitchable deep cavitand. Chem. Commun. 49, 4842–4844 (2013)
Gale, P.A., Sessler, J.L., Král, V., Lynch, V.: Calix[4]pyrroles: old yet new anion-binding agents. J. Am. Chem. Soc. 118, 5140–5141 (1996)
Radu, C., Delmau, L.H., Moyer, B.A., Sessler, J.L., Cho, W.S., Gross, D., Bates, G.W., Brooks, S.J., Light, M.E., Gale, P.A.: Calix[4]pyrrole: an old yet new ion-pair receptor. Angew. Chem. Int. Ed. 44, 2537–2542 (2005)
Sareen, D., Lee, J.H., Hwang, H., Yoo, S., Lee, C.-H.: Ion-mediated single-molecular optical switching and sensing based on the fluorophore-tethered calix[4]pyrrole. Chem. Commun. 52, 5852–5855 (2016)
Aydogan, A., Coady, D.J., Kim, S.K., Akar, A., Bielawski, C.W., Marquez, M., Sessler, J.L.: Poly(methyl methacrylate)s with pendant calixpyrroles and crown ethers: polymeric extractants for potassium halides. Angew. Chem. Int. Ed. 47, 9648–9652 (2008)
Clarke, H.J., Howe, E.N.W., Wu, X., Sommer, F., Yano, M., Light, M.E., Kubik, S., Gale, P.A.: Transmembrane fluoride transport: direct measurement and selectivity studies. J. Am. Chem. Soc. 138, 16515–16522 (2016)
Gu, R., Depraetere, S., Kotek, J., Budka, J., Wagner-Wysiecka, E., Biernat, J.F., Dehaen, W.: Anion recognition by alpha-arylazo-N-confused calix[4]pyrroles. Org. Biomol. Chem. 3, 2921–2923 (2005)
Jain, V.K., Mandalia, H.C.: Azocalix[4]pyrroles: one-pot microwave and one drop water assisted synthesis, spectroscopic characterization and preliminary investigation of its complexation with copper(II). J. Incl. Phenom. Macrocycl. Chem. 63, 27–35 (2008)
Jain, V.K., Mandalia, H.C., Bhojak, N.: Azocalix[4]pyrrole dyes: application in dyeing of fibers and their antimicrobial activity. Fiber. Polym. 11, 363–371 (2010)
Chauhan, S.M.S., Garg, B., Bisht, T.: Synthesis and anion binding of 2-arylazo-meso-octamethylcalix[4]pyrroles. Supramol. Chem. 21, 394–400 (2009)
Sekiya, R., Diaz-Moscoso, A., Ballester, P.: Synthesis and dimerization studies of a lipophilic photoresponsive aryl-extended tetraurea-calix[4]pyrrole. Chem. Eur. J. 24, 2182–2191 (2017)
Garg, B., Bisht, T., Chauhan, S.M.S.: Synthesis and anion binding properties of novel 3,12- and 3,7-bis(4′-nitrophenyl)-azo-calix[4]pyrrole receptors. New J. Chem. 34, 1251–1254 (2010)
Nishiyabu, R., Palacios, M.A., Dehaen, W., Anzenbacher, P. Jr.: Synthesis, structure, anion binding, and sensing by calix[4]pyrrole isomers. J. Am. Chem. Soc. 128, 11496–11504 (2006)
Escobar, L., Arroyave, F.A., Ballester, P.: Synthesis and binding studies of a tetra-α aryl-extended photoresponsive calix[4]pyrrole receptor bearing meso-alkyl substituents. Eur. J. Org. Chem. 2018, 1097–1106 (2018)
Osorio-Planes, L., Espelt, M., Pericàs, M.A., Ballester, P.: Reversible photocontrolled disintegration of a dimeric tetraurea-calix[4]pyrrole capsule with all-trans appended azobenzene units. Chem. Sci. 5, 4260–4264 (2014)
Jain, V.K., Mandalia, H.C., Gupte, H.S., Vyas, D.J.: Azocalix[4]pyrrole Amberlite XAD-2: new polymeric chelating resins for the extraction, preconcentration and sequential separation of Cu(II), Zn(II) and Cd(II) in natural water samples. Talanta 79, 1331–1340 (2009)
Cafeo, G., Kohnke, F.H., Mezzatesta, G., Profumo, A., Rosano, C., Villari, A., White, A.J.: Host-guest chemistry of a bis-calix[4]pyrrole derivative containing a trans/cis-switchable azobenzene unit with several aliphatic bis-carboxylates. Chem. Eur. J. 21, 5323–5327 (2015)
Yuan, K., Dang, J.S., Guo, Y.J., Zhao, X.: Theoretical prediction of the host-guest interactions between novel photoresponsive nanorings and C60: a strategy for facile encapsulation and release of fullerene. J. Comput. Chem. 36, 518–528 (2015)
Kang, H.M., Kim, H.Y., Jung, J.W., Cho, C.G.: Practical synthesis of azobenzenophanes. J. Org. Chem. 72, 679–682 (2007)
Funke, U., Grützmacher, H.-F.: Dithia-diaza[n.2] paracyclophane-enes. Tetrahedron 43, 3787–3795 (1987)
Schmiegel, J., Grützmacher, H.-F.: A macrocyclic 2,19-dioxo[3.3](3,3′) azobenzolophane by transition-metal carbonyl complex-mediated CO insertion and cyclization. Chem. Ber. 123, 1749–1752 (1990)
Wegner, H., Heindl, A., Schweighauser, L., Logemann, C.: Azobenzene macrocycles: synthesis of a Z-stable azobenzenophane. Synthesis 49, 2632–2639 (2017)
Paudler, W.W., Zeiler, A.G.: Diazocine chemistry. VI. Aromaticity of 5,6-dihydrodibenzo[b,f][1,2]diazocine. J. Org. Chem. 34, 3237–3239 (1969)
Tauer, E., Machinek, R.: ortho-Azobenzenophanes: photochemical and thermal reactions of [2,2][2,2′]azobenzenophane. Liehigs Ann. 1996, 1213–1216 (1996)
Siewertsen, R., Neumann, H., Buchheim-Stehn, B., Herges, R., Nather, C., Renth, F., Temps, F.: Highly efficient reversible Z-E photoisomerization of a bridged azobenzene with visible light through resolved S(1)(nπ*) absorption bands. J. Am. Chem. Soc. 131, 15594–15595 (2009)
Bockmann, M., Doltsinis, N.L., Marx, D.: Unraveling a chemically enhanced photoswitch: bridged azobenzene. Angew. Chem. Int. Ed. 49, 3382–3384 (2010)
Carstensen, O., Sielk, J., Schonborn, J.B., Granucci, G., Hartke, B.: Unusual photochemical dynamics of a bridged azobenzene derivative. J. Chem. Phys. 133, 124305 (2010)
Liu, L., Yuan, S., Fang, W.H., Zhang, Y.: Probing highly efficient photoisomerization of a bridged azobenzene by a combination of CASPT2//CASSCF calculation with semiclassical dynamics simulation. J. Phys. Chem. A 115, 10027–10034 (2011)
Bockmann, M., Doltsinis, N.L., Marx, D.: Enhanced photoswitching of bridged azobenzene studied by nonadiabatic ab initio simulation. J. Chem. Phys. 137, 22A505 (2012)
Gao, A.-H., Li, B., Zhang, P.-Y., Han, K.-L.: Nonadiabatic ab initio molecular dynamics of photoisomerization in bridged azobenzene. J. Chem. Phys. 137, 204305 (2012)
Jiang, C.-W., Xie, R.-H., Li, F.-L., Allen, R.E.: Ultrafast cis-to-trans photoisomerization of a bridged azobenzene through nπ∗ excitation: rotational pathway is not restricted. Chem. Phys. Lett. 521, 107–112 (2012)
Cao, J., Liu, L.H., Fang, W.H., Xie, Z.Z., Zhang, Y.: Photo-induced isomerization of ethylene-bridged azobenzene explored by ab initio based non-adiabatic dynamics simulation: a comparative investigation of the isomerization in the gas and solution phases. J. Chem. Phys. 138, 134306 (2013)
Carstensen, N.O.: QM/MM surface-hopping dynamics of a bridged azobenzene derivative. Phys. Chem. Chem. Phys. 15, 15017–15026 (2013)
Fan, G., Liu, J., He, G.: Nonadiabatic dynamics study of bridged-azobenzene by the time-dependent density functional tight-binding method. Comput. Theor. Chem. 1023, 10–18 (2013)
Gao, A.-H., Li, B., Zhang, P.-Y., Liu, J.: Photochemical dynamics simulations for trans–cis photoisomerizations of azobenzene and bridged azobenzene. Comput. Theor. Chem. 1031, 13–21 (2014)
Gao, W., Yu, L., Zheng, X., Lei, Y., Zhu, C., Han, H.: Chiral conversion and periodical decay in bridged-azobenzene photoisomerization: an ab initio on-the-fly nonadiabatic dynamics simulation. RSC Adv. 6, 39542–39552 (2016)
Liu, L., Wang, Y., Fang, Q.: New insights into mechanistic photoisomerization of ethylene-bridged azobenzene from ab initio multiple spawning simulation. J. Chem. Phys. 146, 064308 (2017)
Tamaoki, N., Koseki, K., Yamaoka, T.: [2.2](4,4′)Azobenzenophane. Angew. Chem. Int. Ed. 29, 105–106 (1990)
Tamaoki, N., Ogata, K., Koseki, K., Yamaoka, T.: [2.2](4,4′)Azobenzenophane. Synthesis, structure, and cis-trans isomerization. Tetrahedron 46, 5931–5942 (1990)
Tamaoki, N., Yoshimura, S., Yamaoka, T.: A photochromic memory with a non-destructive read-out property. Thin Solid Films 221, 132–139 (1992)
Hilpert, H., Hoesch, L., Dreiding, A.S.: Reduktion von 1,2-bis[(Z)-(2-nitrophenyl)-NNO-azoxy]benzol: synthese von cyclotrisazobenzol (=(5E,6aZ,11E,12aZ,17E,18aZ)-5,6,11,12,17,18-hexaazatribenzo[aei][1,3,5,7,9,11]cyclododeca-hexaen). Helv. Chim. Acta 68, 325–333 (1985)
Reuter, R., Hostettler, N., Neuburger, M., Wegner, H.A.: Synthesis and property studies of cyclotrisazobenzenes. Eur. J. Org. Chem. 2009, 5647–5652 (2009)
Reuter, R., Wegner, H.A.: Synthesis and isomerization studies of cyclotrisazobiphenyl. Chem. Eur. J. 17, 2987–2995 (2011)
Slavov, C., Yang, C., Schweighauser, L., Wegner, H.A., Dreuw, A., Wachtveitl, J.: Ultrafast excited-state deactivation dynamics of cyclotrisazobenzene-a novel type of UV-B absorber. Chemphyschem 18, 2137–2141 (2017)
Tamaoki, N., Yamaoka, T.: Light-intensity dependence in the photochromism of dibenzo[2.2](4,4)-azobenzenophane. J. Chem. Soc. Perkin Trans. 2 6, 873–878 (1991)
Tamaoki, N., Koseki, K., Yamaoka, T.: The photo- and thermal cis-trans isomerization of (4,4′)azobenzenophane. Tetrahedron Lett. 31, 3309–3312 (1990)
Tamaoki, N., Koseki, K., Yamaoka, T.: Photo- and thermal cis–trans isomerization of (4,4′)azobenzenophane. J. Chem. Soc. Perkin Trans. 2 7, 1107–1110 (1992)
Kawamoto, M., Shiga, N., Takaishi, K., Yamashita, T.: Non-destructive erasable molecular switches and memory using light-driven twisting motions. Chem. Commun. 46, 8344–8346 (2010)
Mathews, M., Zola, R.S., Hurley, S., Yang, D.K., White, T.J., Bunning, T.J., Li, Q.: Light-driven reversible handedness inversion in self-organized helical superstructures. J. Am. Chem. Soc. 132, 18361–18366 (2010)
Joshi, D.K., Mitchell, M.J., Bruce, D., Lough, A.J., Yan, H.: Synthesis of cyclic azobenzene analogues. Tetrahedron 68, 8670–8676 (2012)
Eljabu, F., Dhruval, J., Yan, H.: Incorporation of cyclic azobenzene into oligodeoxynucleotides for the photo-regulation of DNA hybridization. Bioorg. Med. Chem. Lett. 25, 5594–5596 (2015)
Shen, Y.T., Guan, L., Zhu, X.Y., Zeng, Q.D., Wang, C.: Submolecular observation of photosensitive macrocycles and their isomerization effects on host-guest network. J. Am. Chem. Soc. 131, 6174–6180 (2009)
Nagamani, S.A., Norikane, Y., Tamaoki, N.: Photoinduced hinge-like molecular motion: studies on xanthene-based cyclic azobenzene dimers. J. Org. Chem. 70, 9304–9313 (2005)
Fridkin, G., Gilon, C.: Azo cyclization: peptide cyclization via azo bridge formation. J. Pept. Res. 60, 104–111 (2002)
Norikane, Y., Kitamoto, K., Tamaoki, N.: [1.1](3,3′)-azobenzenophane: novel crystal structure and cis–trans isomerization of distorted azobenzene. Org. Lett. 4, 3907–3910 (2002)
Rau, H., Rötger, D.: Photochromic azobenzenes which are stable in the trans and cis forms. Mol. Cryst. Liq. Crysr. 246, 143–146 (1994)
Röttger, D., Rau, H.: Photochemistry of azobenzenophanes with three-membered bridges. J. Photochem. Photobiol. A Chem. 101, 205–214 (1996)
Norikane, Y., Kitamoto, K., Tamaoki, N.: Novel crystal structure, cis-trans isomerization, and host property of meta-substituted macrocyclic azobenzenes with the shortest linkers. J. Org. Chem. 68, 8291–8304 (2003)
Norikane, Y., Hirai, Y., Yoshida, M.: Photoinduced isothermal phase transitions of liquid-crystalline macrocyclic azobenzenes. Chem. Commun. 47, 1770–1772 (2011)
Reuter, R., Wegner, H.A.: Switchable 3D networks by light controlled pi-stacking of azobenzene macrocycles. Chem. Commun. 49, 146–148 (2013)
Gräf, D., Nitsch, H., Ufermann, D., Sawitzki, G., Patzelt, H., Rau, H.: Azobenzene phanes. Angew. Chem. Int. Ed. 21, 373–374 (1982)
Rau, H., Lueddecke, E.: On the rotation-inversion controversy on photoisomerization of azobenzenes. Experimental proof of inversion. J. Am. Chem. Soc. 104, 1616–1620 (1982)
Ritter, G., Haefelinger, G., Lueddecke, E., Rau, H.: Tetrazetidine: ab initio calculations and experimental approach. J. Am. Chem. Soc. 111, 4627–4635 (1989)
Rau, H., Waldner, I.: A non-rotatory isomerization path in ethene derivatives? Investigation of a stilbenophane and protonated azobenzenophanes (“pseudo-stilbenophanes”). Phys. Chem. Chem. Phys. 4, 1776–1780 (2002)
Ciminelli, C., Granucci, G., Persico, M.: Are azobenzenophanes rotation-restricted? J. Chem. Phys. 123, 174317 (2005)
Lu, Y.C., Diau, E.W., Rau, H.: Femtosecond fluorescence dynamics of rotation-restricted azobenzenophanes: new evidence on the mechanism of trans⟶cis photoisomerization of azobenzene. J. Phys. Chem. A 109, 2090–2099 (2005)
Hombrecher, H.K., Lüdtke, K.: Synthesis and spectroscopic investigation of directly azobenzene bridged diporphyrins. Tetrahedron 49, 9489–9494 (1993)
Goulet-Hanssens, A., Utecht, M., Mutruc, D., Titov, E., Schwarz, J., Grubert, L., Bleger, D., Saalfrank, P., Hecht, S.: Electrocatalytic Z⟶E isomerization of azobenzenes. J. Am. Chem. Soc. 139, 335–341 (2017)
Pieraccini, S., Gottarelli, G., Labruto, R., Masiero, S., Pandoli, O., Spada, G.P.: The control of the cholesteric pitch by some azo photochemical chiral switches. Chem. Eur. J. 10, 5632–5639 (2004)
Müri, M., Schuermann, K.C., De Cola, L., Mayor, M.: Shape-switchable azo-macrocycles. Eur. J. Org. Chem. 2009, 2562–2575 (2009)
Tanaka, K., Fukuoka, S., Miyanishi, H., Takahashi, H.: Novel chiral Schiff base macrocycles containing azobenzene chromophore: gelation and guest inclusion. Tetrahedron Lett. 51, 2693–2696 (2010)
Cram, D.J., Carmack, R.A., Helgeson, R.C.: Host-guest complexation. 45. A highly preorganized chromogenic spherand indicator system specific for sodium and lithium ions. J. Am. Chem. Soc. 110, 571–577 (1988)
Uchida, E., Sakaki, K., Nakamura, Y., Azumi, R., Hirai, Y., Akiyama, H., Yoshida, M., Norikane, Y.: Control of the orientation and photoinduced phase transitions of macrocyclic azobenzene. Chem. Eur. J. 19, 17391–17397 (2013)
Bassotti, E., Carbone, P., Credi, A., Di Stefano, M., Masiero, S., Negri, F., Orlandi, G., Spada, G.P.: Effect of strain on the photoisomerization and stability of a congested azobenzenophane: a combined experimental and computational study. J. Phys. Chem. A 110, 12385–12394 (2006)
Dittrich, U., Grützmacher, H.F.: 2-Thia-10,11-diaza[3.2]metacyclophan-10-en. Chem. Ber. 118, 4404–4414 (1985)
Norikane, Y., Katoh, R., Tamaoki, N.: Unconventional thermodynamically stable cis isomer and trans to cis thermal isomerization in reversibly photoresponsive [0.0](3,3′)-azobenzenophane. Chem. Commun. 16, 1898–1900 (2008)
Autret, M., Le Plouzennec, M., Moinet, C., Simonneaux, G.: Intramolecular fluorescence quenching in azobenzene-substituted porphyrins. J. Chem. Soc. Chem. Commun. 10, 1169 (1994)
Hombrecher, H.K., Ldtke, K., Koll, D.: Synthesis and electrochemical investigation of azobenzene-substituted porphyrins. J. Prakt. Chem. 338, 257–263 (1996)
Liu, X., Feng, Y., Zhao, Y., Chen, H., Li, X.: Synthesis, characterization and spectroscopic investigation of azo-porphyrins. Dyes Pigm. 75, 413–419 (2007)
Huang, W., Lee, S.K., Sung, Y.M., Peng, F., Yin, B., Ma, M., Chen, B., Liu, S., Kirk, S.R., Kim, D., Song, J.: Azobenzene-bridged porphyrin nanorings: syntheses, structures, and photophysical properties. Chem. Eur. J. 21, 15328–15338 (2015)
Neumann, K.H., Vögtle, F.: Isomeric double decker porphyrins bridged by four azobenzene units. J. Chem. Soc. Chem. Commun. 8, 520–522 (1988)
Hunter, C.A., Sarson, L.D.: Azobenzene-porphyrins. Tetrahedron Lett. 37, 699–702 (1996)
Chiu, K.Y., Tu, Y.-J., Lee, C.-J., Yang, T.-F., Lai, L.-L., Chao, I., Su, Y.O.: Unusual spectral and electrochemical properties of azobenzene-substituted porphyrins. Electrochim. Acta 62, 51–62 (2012)
Yamamura, T., Momotake, A., Arai, T.: Synthesis and photochemical properties of porphyrin–azobenzene triad. Tetrahedron Lett. 45, 9219–9223 (2004)
Muraoka, T., Kinbara, K., Aida, T.: Mechanical twisting of a guest by a photoresponsive host. Nature 440, 512–515 (2006)
Muraoka, T., Kinbara, K., Wakamiya, A., Yamaguchi, S., Aida, T.: Crystallographic and chiroptical studies on tetraarylferrocenes for use as chiral rotary modules for molecular machines. Chem. Eur. J. 13, 1724–1730 (2007)
Tsuchiya, S.: Intramolecular electron transfer of diporphyrins comprised of electron-deficient porphyrin and electron-rich porphyrin with photocontrolled isomerization. J. Am. Chem. Soc. 121, 48–53 (1999)
Amaravathi, M., Kanakaraju, S., Chandramouli, G.V.P.: Synthesis and characterization of azobenzene–porphyrins. J. Heterocycl. Chem. 50, 268–271 (2013)
Esdaile, L.J., Jensen, P., McMurtrie, J.C., Arnold, D.P.: Azoporphyrin: the porphyrin analogue of azobenzene. Angew. Chem. Int. Ed. 46, 2090–2093 (2007)
Oka, Y., Tamaoki, N.: Structure of silver(I) complex prepared from azobenzenonaphthalenophane, photochemical coordination change of silver(I) and silver(I)-induced acceleration of Z-E thermal isomerization of azobenzene unit. Inorg. Chem. 49, 4765–4767 (2010)
Lu, J., Jiang, G., Zhang, Z., Zhang, W., Yang, Y., Wang, Y., Zhou, N., Zhu, X.: A cyclic azobenzenophane-based smart polymer for chiroptical switches. Polym. Chem. 6, 8144–8149 (2015)
Takaishi, K., Kawamoto, M.: Synthesis and conformation of substituted chiral binaphthyl-azobenzene cyclic dyads with chiroptical switching capabilities. Molecules 16, 1603–1624 (2011)
Takaishi, K., Kawamoto, M., Tsubaki, K., Wada, T.: Photoswitching of dextro/levo rotation with axially chiral binaphthyls linked to an azobenzene. J. Org. Chem. 74, 5723–5726 (2009)
Takaishi, K., Kawamoto, M., Tsubaki, K., Furuyama, T., Muranaka, A., Uchiyama, M.: Helical chirality of azobenzenes induced by an intramolecular chiral axis and potential as chiroptical switches. Chem. Eur. J. 17, 1778–1782 (2011)
Azov, V.A., Cordes, J., Schluter, D., Dulcks, T., Bockmann, M., Doltsinis, N.L.: Light-controlled macrocyclization of tetrathiafulvalene with azobenzene: designing an optoelectronic molecular switch. J. Org. Chem. 79, 11714–11721 (2014)
Basheer, M.C., Oka, Y., Mathews, M., Tamaoki, N.: A light-controlled molecular brake with complete ON-OFF rotation. Chem. Eur. J. 16, 3489–3496 (2010)
Reuter, R., Wegner, H.A.: A chiral cyclotrisazobiphenyl: synthesis and photochemical properties. Org. Lett. 13, 5908–5911 (2011)
Mathews, M., Tamaoki, N.: Planar chiral azobenzenophanes as chiroptic switches for photon mode reversible reflection color control in induced chiral nematic liquid crystals. J. Am. Chem. Soc. 130, 11409–11416 (2008)
Hashim, P.K., Basheer, M.C., Tamaoki, N.: Chirality induction by E–Z photoisomerization in [2,2]paracyclophane-bridged azobenzene dimer. Tetrahedron Lett. 54, 176–178 (2013)
Thomas, R., Yoshida, Y., Akasaka, T., Tamaoki, N.: Influence of a change in helical twisting power of photoresponsive chiral dopants on rotational manipulation of micro-objects on the surface of chiral nematic liquid crystalline films. Chem. Eur. J. 18, 12337–12348 (2012)
Thomas, R., Tamaoki, N.: Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element. Beilstein J. Org. Chem. 12, 2211–2215 (2016)
Despras, G., Hain, J., Jaeschke, S.O.: Photocontrol over molecular shape: synthesis and photochemical evaluation of glycoazobenzene macrocycles. Chem. Eur. J. 23, 10838–10847 (2017)
Jousselme, B., Blanchard, P., Allain, M., Levillain, E., Dias, M., Roncali, J.: Structural control of the electronic properties of photodynamic azobenzene-derivatized pi-conjugated oligothiophenes. J. Phys. Chem. A 110, 3488–3494 (2006)
Takaishi, K., Kawamoto, M., Muranaka, A., Uchiyama, M.: Fusion of photochromic reaction and synthetic reaction: photoassisted cyclization to highly strained chiral azobenzenophanes. Org. Lett. 14, 3252–3255 (2012)
Takaishi, K., Muranaka, A., Kawamoto, M., Uchiyama, M.: Planar chirality of twisted trans-azobenzene structure induced by chiral transfer from binaphthyls. J. Org. Chem. 76, 7623–7628 (2011)
Takaishi, K., Muranaka, A., Kawamoto, M., Uchiyama, M.: Photoinversion of cisoid/transoid binaphthyls. Org. Lett. 14, 276–279 (2012)
Losensky, H.-W., Spelthann, H., Ehlen, A., Vögtle, F., Bargon, J.: A novel tris(azo)macrobicyclic molecule-synthesis, photochemistry, and isomer separation. Angew. Chem. Int. Ed. 27, 1189–1191 (1988)
Deo, C., Bogliotti, N., Metivier, R., Retailleau, P., Xie, J.: A visible-light-triggered conformational diastereomer photoswitch in a bridged azobenzene. Chem. Eur. J. 22, 9092–9096 (2016)
Lu, H.B., Xie, X.Y., Xing, J., Xu, C., Wu, Z.Q., Zhang, G.B., Lv, G.Q., Qiu, L.Z.: Wavelength-tuning and band-broadening of a cholesteric liquid crystal induced by a cyclic chiral azobenzene compound. Opt. Mater. Express 6, 3145–3158 (2016)
Kerner, L., Kickova, A., Filo, J., Kedzuch, S., Putala, M.: Elucidation of photoisomerization-related structural changes in an acrylamide-bridged binaphthalene-diazene macrocyclic chiroptical switch by experimental electronic circular dichroism spectra simulation: role of dispersion corrections. J. Phys. Chem. A 119, 8588–8598 (2015)
Kawamoto, M., Aoki, T., Wada, T.: Light-driven twisting behaviour of chiral cyclic compounds. Chem. Commun. 9, 930–932 (2007)
Nunzi, J.-M., Kawamoto, M., Aoki, T., Wada, T.: Photoinduced twisting behavior of chiral cyclic compounds. In: Proceeding of Linear and Nonlinear Optics of Organic Materials, vol. 6653, pp. 66530K (2007)
Xu, X., Zhou, N., Zhu, J., Tu, Y., Zhang, Z., Cheng, Z., Zhu, X.: The first example of main-chain cyclic azobenzene polymers. Macromol. Rapid Commun. 31, 1791–1797 (2010)
Jiang, X., Lu, J., Zhou, F., Zhang, Z., Pan, X., Zhang, W., Wang, Y., Zhou, N., Zhu, X.: Molecularly-defined macrocycles containing azobenzene main-chain oligomers: modular stepwise synthesis, chain-length and topology-dependent properties. Polym. Chem. 7, 2645–2651 (2016)
Sun, Y., Wang, Z., Li, Y., Zhang, Z., Zhang, W., Pan, X., Zhou, N., Zhu, X.: Photoresponsive amphiphilic macrocycles containing main-chain azobenzene polymers. Macromol. Rapid Commun. 36, 1341–1347 (2015)
Zhang, Y., Zhu, X., Zhou, N., Chen, X., Zhang, W., Yang, Y., Zhu, X.: Cyclic main-chain phenylazo naphthalene polymers: topological effect on fluorescence emission and photoinduced surface relief grating formation. Chem. Asian J. 7, 2217–2221 (2012)
Ding, L., Song, W., Jiang, R., Zhu, L.: Macrocycle-based topological azo-polymers: facile synthesis and unusual photoresponsive properties. Polym. Chem. 8, 7133–7142 (2017)
Li, J., Zhou, N., Zhang, Z., Xu, Y., Chen, X., Tu, Y., Hu, Z., Zhu, X.: A smart cyclic azobenzene as pendant groups on polymer chains: topological effect of the cyclization on thermal and photoresponsive properties of the azobenzene and the polymer. Chem. Asian J. 8, 1095–1100 (2013)
Sheng, Y., Yu, C., Zhou, C., Xu, L., Wu, J., Wang, J., Chen, X.: All-optical fabrication of blazed grating on Pcyclic-azoMMA film. Proc. SPIE 9271, 927121 (2014)
Chen, B., Wang, Z., Lu, J., Yang, X., Wang, Y., Zhang, Z., Zhu, J., Zhou, N., Li, Y., Zhu, X.: Cyclic azobenzene-containing amphiphilic diblock copolymers: solution self-assembly and unusual photo-responsive behaviors. Polym. Chem. 6, 3009–3013 (2015)
Lu, J., Xia, A., Zhou, N., Zhang, W., Zhang, Z., Pan, X., Yang, Y., Wang, Y., Zhu, X.: A versatile cyclic 2,2′-azobenzenophane with a functional handle and its polymers: efficient synthesis and effect of topological structure on chiroptical properties. Chem. Eur. J. 21, 2324–2329 (2015)
Jiang, G., Li, L., Xu, X., Lu, J., Zhu, X., Zhang, Z., Zhou, N., Zhu, X.: The synthesis and photoactive properties of cyclic amphiphilic polymers with azobenzene in main chain. J. Polym. Sci. A 54, 1834–1841 (2016)
Lu, J., Zhou, F., Li, L., Zhang, Z., Meng, F., Zhou, N., Zhu, X.: Novel cyclic azobenzene-containing vesicles: photo/reductant responsiveness and potential applications in colon disease treatment. RSC Adv. 6, 58755–58763 (2016)
Cai, Y., Lu, J., Zhou, F., Zhou, X., Zhou, N., Zhang, Z., Zhu, X.: Cyclic amphiphilic random copolymers bearing azobenzene side chains: facile synthesis and topological effects on self-assembly and photoisomerization. Macromol. Rapid Commun. 35, 901–907 (2014)
Han, D., Tong, X., Zhao, Y., Galstian, T., Zhao, Y.: Cyclic azobenzene-containing side-chain liquid crystalline polymers: synthesis and topological effect on mesophase transition, order, and photoinduced birefringence. Macromolecules 43, 3664–3671 (2010)
Li, L., Cai, Y., Zhang, Z., Zhang, W., Zhou, N., Zhu, X.: Photoresponsive amphiphilic block macrocycles bearing azobenzene side chains. RSC Adv. 7, 38335–38341 (2017)
Zhang, H., Zhou, N., Zhu, X., Chen, X., Zhang, Z., Zhang, W., Zhu, J., Hu, Z., Zhu, X.: Cyclic side-chain phenylazo naphthalene polymers: enhanced fluorescence emission and surface relief grating formation. Macromol. Rapid Commun. 33, 1845–1851 (2012)
Vögtle, F., Müller, W.M., Müller, U., Bauer, M., Rissanen, K.: Photoswitchable catenanes. Angew. Chem. Int. Ed. 32, 1295–1297 (1993)
Bauer, M., Manfred Müller, W., Müller, U., Rissanen, K., Vögtle, F.: Azobenzene-based photoswitchable catenanes. Liehigs Ann. 1995, 649–656 (1995)
Tang, H.-S., Zhu, N., Yam, V.W.-W.: Tetranuclear macrocyclic gold(I) alkynyl phosphine complex containing azobenzene functionalities: a dual-input molecular logic with photoswitching behavior controllable via silver(I) coordination/decoordination. Organometallics 26, 22–25 (2007)
Ryan, S.T., Del Barrio, J., Suardiaz, R., Ryan, D.F., Rosta, E., Scherman, O.A.: A dynamic and responsive host in action: light-controlled molecular encapsulation. Angew. Chem. Int. Ed. 55, 16096–16100 (2016)
Norikane, Y., Tamaoki, N.: Light-driven molecular hinge: a new molecular machine showing a light-intensity-dependent photoresponse that utilizes the trans-cis isomerization of azobenzene. Org. Lett. 6, 2595–2598 (2004)
Rajakumar, P., Senthilkumar, B., Srinivasan, K.: Synthesis of azobenzenophanes with a large molecular cavity. Aust. J. Chem. 59, 75–77 (2006)
Heberlein, M., Kobayashi, S., Skrabal, P.: Synthese von 17,18,19,20-tetrahydro- und18,19-dioxo-17,18,19,20-tetrahydrotribenzo [c,g,m]-[1,2,5,6,9,12]hexaazacyclotetradecinohne Anwendung des Metalltemplat-Effektes. Synthesis 1979, 545–546 (1979)
Yamamura, M., Okazaki, Y., Nabeshima, T.: Photoisomerization locking of azobenzene by formation of a self-assembled macrocycle. Chem. Commun. 48, 5724–5726 (2012)
Gargiulli, C., Gattuso, G., Notti, A., Pappalardo, S., Parisi, M.F., Puntoriero, F.: Photoisomerizable azobenzene-containing oxacalixarenes. Tetrahedron Lett. 53, 616–619 (2012)
Nokubi, T., Kindt, S., Clark, T., Kamimura, A., Heinrich, M.R.: Synthesis of dibenzo[c,e][1,2]diazocines—a new group of eight-membered cyclic azo compounds. Tetrahedron Lett. 56, 316–320 (2015)
Kaneda, T., Umeda, S., Tanigawa, H., Misumi, S., Kai, Y., Morii, H., Miki, K., Kasai, N.: A spherand azophenol dye: lithium ion specific coloration with “perfect” selectivity. J. Am. Chem. Soc. 107, 4802–4803 (1985)
Chertanova, L., Pascard, C., Sheremetev, A.: New macrocyclic ligands. X-ray study of three macrocycles involving azofurazan subunit. Supramol. Chem. 3, 71–78 (1993)
Schweighauser, L., Wegner, H.A.: Cyclotetraazocarbazole—a multichromic molecule. Chem. Commun. 49, 4397–4399 (2013)
Commins, P., Garcia-Garibay, M.A.: Photochromic molecular gyroscope with solid state rotational states determined by an azobenzene bridge. J. Org. Chem. 79, 1611–1619 (2014)
Maciejewski, J., Sobczuk, A., Claveau, A., Nicolai, A., Petraglia, R., Cervini, L., Baudat, E., Mieville, P., Fazzi, D., Corminboeuf, C., Sforazzini, G.: Photochromic torsional switch (PTS): a light-driven actuator for the dynamic tuning of pi-conjugation extension. Chem. Sci. 8, 361–365 (2017)
Behrendt, R., Schenk, M., Musiol, H.-J., Moroder, L.: Photomodulation of conformational states. Synthesis of cyclic peptides with backbone-azobenzene moieties. J. Pept. Sci. 5, 519–529 (1999)
Karp, E., Pecinovsky, C.S., McNevin, M.J., Gin, D.L., Schwartz, D.K.: Langmuir monolayers of a photoisomerizable macrocycle surfactant. Langmuir 23, 7923–7927 (2007)
Adam, A., Haberhauer, G.: Switching process consisting of three isomeric states of an azobenzene unit. J. Am. Chem. Soc. 139, 9708–9713 (2017)
Muraoka, T., Kinbara, K., Kobayashi, Y., Aida, T.: Light-driven open-close motion of chiral molecular scissors. J. Am. Chem. Soc. 125, 5612–5613 (2003)
Muraoka, T., Kinbara, K., Aida, T.: Reversible operation of chiral molecular scissors by redox and UV light. Chem. Commun. 14, 1441–1443 (2007)
Ulysse, L., Cubillos, J., Chmielewski, J.: Photoregulation of cyclic peptide conformation. J. Am. Chem. Soc. 117, 8466–8467 (1995)
Sun, S.-S., Anspach, J.A., Lees, A.J.: Self-assembly of transition-metal-based macrocycles linked by photoisomerizable ligands: examples of photoinduced conversion of tetranuclear–dinuclear squares. Inorg. Chem. 41, 1862–1869 (2002)
Pecinovsky, C.S., Hatakeyama, E.S., Gin, D.L.: Polymerizable photochromic macrocyclic metallomesogens: design of supramolecular polymers with responsive nanopores. Adv. Mater. 20, 174–178 (2008)
Haberhauer, G., Kallweit, C., Wolper, C., Blaser, D.: An azobenzene unit embedded in a cyclopeptide as a type-specific and spatially directed switch. Angew. Chem. Int. Ed. 52, 7879–7882 (2013)
Lin, C., Maisonneuve, S., Metivier, R.,Xie, J.: Photoswitchable Carbohydrate-Based Macrocyclic Azobenzene: Synthesis, Chiroptical Switching, and Multistimuli-Responsive Self-Assembly. Chem. Eur. J. 23, 14996–15001 (2017)
Haberhauer, G., Kallweit, C.: A bridged azobenzene derivative as a reversible, light-induced chirality switch. Angew. Chem. Int. Ed. 49, 2418–2421 (2010)
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This work was supported by NSFC (21672112), the Fundamental Research Funds for the Central Universities and Program of Tianjin Young Talents, which are gratefully acknowledged.
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Geng, WC., Sun, H. & Guo, DS. Macrocycles containing azo groups: recognition, assembly and application. J Incl Phenom Macrocycl Chem 92, 1–79 (2018). https://doi.org/10.1007/s10847-018-0819-8
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DOI: https://doi.org/10.1007/s10847-018-0819-8