Abstract
This article presents a brief overview of recent advances in azo-containing supramolecular systems. In literature, it has been shown that azo supramolecular polymers and their composite materials exhibit fast and intelligent responses to various external stimuli, such as temperature, pH change, redox reagents, ligands, coupling reagents, etc. In applications, these systems are widely used for molecular motors, shape memory, liquid crystal, solar thermal energy storage, signal transmission, intelligent encryption, and other purposes. Furthermore, these systems can function as key components for device upgrade processing. However, the design and rules of azo supramolecular polymers are still not supported by an exact theory. Information about the relationship between the spatial structure and behavior is lacking, and new supramolecular materials cannot be designed by adding functional moieties to known azo polymers. Based on the current research status, this review mainly summarizes the structural design principles as well as structures and applications of known azo supramolecules; meanwhile, it highlights the emerging development fields, recent advances, and prospects in fabricating self-assembling intelligent supramolecular systems with azo supramolecular polymers as responsive units. The goal of this review is to bring new inspiration to researchers who want to optimize the chemical structure, steric conformation, electrostatic environment, and specific molecular functionalization.
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References
Lehn, J. M. Supramolecular chemistry-scope and perspectives molecules, supermolecules, and molecular devices (Nobel Lecture). Angew. Chem. Int. Ed. 1988, 27, 89–112.
Yagai, S.; Karatsu, T.; Kitamura, A. Photocontrollable self-assembly. Chem. Eur. J. 2005, 11, 4054–4063.
Cheng, M. J.; Zhang, Q.; Shi, F. Macroscopic supramolecular assembly and its applications. Chinese J. Polym. Sci. 2018, 36, 306–321.
Cao, C.; Li, Y.; Feng Y. Y.; Long, P.; An, H. R.; Qin, C. Q.; Han, J. K.; Li, S. W.; Feng, W. A sulfonimide-based alternating copolymer as a single-ion polymer electrolyte for highperformance lithium-ion batteries. J. Mater. Chem. A2017, 5, 22519–22526.
Archut, A.; Vögtle, F.; De Cola, L.; Azzellini, G. C.; Balzani, V.; Ramanujam, P. S.; Berg, R. H. Azobenzene functionalized cascade molecules: Photoswitchable supramolecular systems. Chem. Eur. J. 1998, 4, 699–706.
Fabbrizzi, L.; Poggi, A. Sensors and switches from supra-molecular chemistry. Chem. Soc. Rev. 1995, 24, 197–202.
Lehn, J. M. Supramolecular chemistry: Receptors, catalysts, and carriers. Science1985, 227, 849–856.
Chu, Z.; Han, Y.; Bian, T.; De, S.; Král, P.; Klajn, R. Supra-molecular control of azobenzene switching on nanoparticles. J. Am. Chem. Soc. 2018, 141, 1949–1960.
Ma, X.; Zhao, Y. Biomedical applications of supramolecular systems based on host-guest interactions. Chem. Rev.2014, 115, 7794–7839.
Mattia, E.; Otto, S. Supramolecular systems chemistry. Natt. Nanotech.2015, 10, 111.
Gilday, L. C.; Robinson, S. W.; Barendt, T. A.; Langton, M. J.; Mullaney, B. R.; Beer, P. D. Halogen bonding in supra-molecular chemistry. Chem. Rev.2015, 115, 7118–7195.
Lehn, J. M. Supramolecular chemistry: Where from? Where to? Chem. Soc. Rev.2017, 46, 2378–2379.
Delbianco, M.; Bharate, P.; Varela-Aramburu, S.; Seeberger, P. H. Carbohydrates in supramolecular chemistry. Chem. Rev.2015, 116, 1693–1752.
Zeng, F.; Zimmerman, S. C. Dendrimers in supramolecular chemistry: From molecular recognition to self-assembly. Chem. Rev.1997, 97, 1681–1712.
Huang, F.; Scherman, O. A. Supramolecular polymers. Chem. Soc. Rev.2012, 41, 5879–5880.
Stupp, S. I.; Keser, M.; Tew, G. N. Functionalized supramolecular materials. Polymer1998, 39, 4505–4508.
Bernhardt, P. V. A supramolecular synthon for H-bonded transition metal arrays. Inorg. Chem.1999, 38, 3481–3483.
Liu, Z. F.; Hashimoto, K.; Fujishima, A. Photoelectrochemical information storage using an azobenzene derivative. Nature1990, 347, 658.
Freundlich, H.; Heller, W. The adsorption of cis- and trans-azobenzene. J. Am. Chem. Soc.1939, 61, 2228–2230.
Kumar, S.; Dinesha, P.; Rosen, M. A. Effect of injection pressure on the combustion, performance and emission characteristics of a biodiesel engine with cerium oxide nanoparticle additive. Energy2019, 185, 1163–1173.
Hartley, G. S. The cis-form of azobenzene. Nature1937, 140, 281.
Gauglitz, G.; Hubig, S. Chemical actinometry in the UV by azobenzene in concentrated solution: A convenient method. J. Photochem1985, 30, 121–125.
Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Artificial molecular machines. Angew. Chem. Int. Ed.2000, 99, 3348–3391.
Ueno, A.; Yoshimura, H.; Saka, R.; Osa, T. Photocontrol of binding ability of capped cyclodextrin. J. Am. Chem. Soc.1979, 101, 2779–2780.
Emoto, A.; Uchida, E.; Fukuda, T. Optical and physical applications of photocontrollable materials: Azobenzene-containing and liquid crystalline polymers. Polymers2012, 4, 150–186.
Tejedor, R. M.; Oriol, L.; Serrano, J. L.; Partal Ureña, F.; López González, J. J. Photoinduced chiral nematic organization in an achiral glassy nematic azopolymer. Adv. Funct. Mater.2007, 17, 3486–3492.
Priewisch, B.; Rück-Braun, K. Efficient preparation of nitrosoarenes for the synthesis of azobenzenes. J. Org. Chem.2005, 70, 2350–2352.
Feng, W.; Luo, W.; Feng, Y. Photo-responsive carbon nanomaterials functionalized by azobenzene moieties: Structures, properties and application. Nanoscale2012, 4, 6118–6134.
Beharry, A. A.; Woolley, G. A. Azobenzene photoswitches for biomolecules. Chem. Soc. Rev.2011, 40, 4422–4437.
Goulet-Hanssens, A.; Barrett, C. J. Photo-control of biological systems with azobenzene polymers. J. Polym. Sci., Part A: Polym. Chem.2013, 51, 3058–3070.
Dong, R.; Liu, Y.; Zhou, Y.; Yan, D.; Zhu, X. Photo-reversible supramolecular hyperbranched polymer based on host-guest interactions. Polym. Chem.2011, 2, 2771–2774.
Qin, M.; Xu, Y.; Cao, R.; Feng, W.; Chen, L. Efficiently controlling the 3D thermal conductivity of a polymer nanocomposite via a hyperelastic double-continuous network of graphene and sponge. Adv. Funct. Mater.2018, 28, 1805053.
Poutanen, M.; Ikkala, O.; Priimagi, A. Structurally controlled dynamics in azobenzene-based supramolecular self-assemblies in solid state. Macromolecules2016, 49, 4095–4101.
Vapaavuori, J.; Ras, R. H.; Kaivola, M.; Bazuin, C. G.; Priimagi, A. From partial to complete optical erasure of azobenzene-polymer gratings: Effect of molecular weight. J. Mater. Chem. C2015, 3, 11011–11016.
Wie, J. J.; Wang, D. H.; Lee, K. M.; White, T. J.; Tan, L. S. The contribution of hydrogen bonding to the photomechanical response of azobenzene-functionalized polyamides. J. Mater. Chem. C2018, 6, 5964–5974.
Oscurato, S. L.; Salvatore, M.; Maddalena, P.; Ambrosio, A. From nanoscopic to macroscopic photo-driven motion in azobenzene-containing materials. Nanophotonics2018, 7, 1387–1422.
Yagai, S.; Nakajima, T.; Karatsu, T.; Saitow, K. I.; Kitamura, A. Phototriggered self-assembly of hydrogen-bonded rosette. J. Am. Chem. Soc.2004, 126, 11500–11508.
Zhan, T. G.; Lin, M. D.; Wei, J.; Liu, L. J.; Yun, M. Y.; Wu, L; Zheng, S. T.; Yin, H. H.; Li, C. K.; Zhang, K. D. Visible-light responsive hydrogen-bonded supramolecular polymers based on ortho-tetrafluorinated azobenzene. Polym. Chem.2017, 8, 7384–7389.
Groombridge, A. S.; Palma, A.; Parker, R. M.; Abell, C.; Scherman, O. A. Aqueous interfacial gels assembled from small molecule supramolecular polymers. Chem. Sci.2017, 8, 1350–1355.
Du, M.; Li, L.; Zhang, J.; Li, K.; Cao, M.; Mo, L.; Hua, G.; Chen, Y.; Yu, H.; Yang, H. Photoresponsive iodine-bonded liquid crystals based on azopyridine derivatives with a low phase-transition temperature. Liquid Crystals2019, 46, 37–44.
Chen, Y.; Yu, H.; Zhang, L.; Yang, H.; Lu, Y. Photoresponsive liquid crystals based on halogen bonding of azopyridines. Chem. Commun.2014, 50, 9647–9649.
Wei, P.; Yan, X.; Huang, F. Supramolecular polymers constructed by orthogonal self-assembly based on host-guest and metal-ligand interactions. Chem. Soc. Rev.2015, 44, 815–832.
Zhou, W.; Kobayashi, T.; Zhu, H.; Yu, H. Electrically conductive hybrid nanofibers constructed with two amphiphilic salt components. Chem. Commun.2011, 47, 12768–12770.
Gao, J.; He, Y.; Xu, H.; Song, B.; Zhang, X.; Wang, Z.; Wang, X. Azobenzene-containing supramolecular polymer films for laser-induced surface relief gratings. Chem. Mater.2007, 19, 14–17.
Cui, L.; Zhao, Y. Azopyridine side chain polymers: An efficient way to prepare photoactive liquid crystalline materials through self-assembly. Chem. Mater.2004, 16, 2076–2082.
Shibaev, P. V.; Schaumburg, K.; Plaksin, V. Responsive chiral hydrogen-bonded polymer composites. Chem. Mater.2002, 14, 959–961.
Zettsu, N.; Ogasawara, T.; Mizoshita, N.; Nagano, S.; Seki, T. Photo-triggered surface relief grating formation in supra-molecular liquid crystalline polymer systems with detachable azobenzene unit. Adv. Mater.2008, 20, 516–521.
Li, S.; Feng, Y.; Long, P.; Qin, C.; Feng, W. The light-switching conductance of an anisotropic azobenzene-based polymer close-packed on horizontally aligned carbon nanotubes. J. Mater. Chem. C2017, 5, 5068–5075.
Hu, Y.; Wu, K. Y.; Zhu, T.; Shen, P.; Zhou, Y.; Li, X.; Wang, C. L.; Tu, Y.; Li, C. Y. Unique supramolecular liquid-crystal phases with different two-dimensional crystal layers. Angew. Chem.2018, 130, 13642–13646.
Huang, C. W.; Ji, W. Y.; Kuo, S. W. Stimuli-eesponsive supramolecular conjugated polymer with phototunable surface relief grating. Polym. Chem.2018, 9, 2813–2820.
Mosciatti, T.; Bonacchi, S.; Gobbi, M.; Ferlauto, L.; Liscio, F.; Giorgini, L.; Orgiu, E.; Samorì, P. Optical input/electrical output memory elements based on a liquid crystalline azobenzene polymer. ACS Appl. Mater. Interface2016, 8, 6563–6569.
Jansze, S. M.; Cecot, G.; Severin, K. Reversible disassembly of metallasupramolecular structures mediated by a metastable-state photoacid. Chem. Sci.2018, 9, 4253–4257.
Park, J.; Feng, D.; Yuan, S.; Zhou, H. C. Photochromic metal-organic frameworks: Reversible control of singlet oxygen generation. Angew. Chem. Int. Ed.2015, 54, 430–435.
Vapaavuori, J.; Bazuin, C. G.; Priimagi, A. Supramolecular design principles for efficient photoresponsive polymer-azobenzene complexes. J. Mater. Chem. C2018, 6, 2168–2188.
Wang, L.; Yin, L.; Zhang, W.; Zhu, X.; Fujiki, M. Circularly polarized light with sense and wavelengths to regulate azobenzene supramolecular chirality in optofluidic medium. J. Am. Chem. Soc.2017, 139, 13218–13226.
Cui, Y.; Gong, H.; Wang, Y.; Li, D.; Bai, H. A thermally insulating textile inspired by polar bear hair. Adv. Mater.2018, 30, 1706807.
Li, Z. Y.; Chen, Y.; Wu, H.; Liu, Y. Photoinduced assembly/disassembly of supramolecular nanoparticle based on polycationic cyclodextrin and azobenzene-containing surfactant. Chemistry Select2018, 3, 3203–3207.
Yu, H.; Liu, H.; Kobayashi, T. Fabrication and photoresponse of supramolecular liquid-crystalline microparticles. ACS Appl. Mater. Interface2011, 3, 1333–1340.
Sun, Z.; Huang, Q.; He, T.; Li, Z.; Zhang, Y.; Yi, L. Multistimuli-responsive supramolecular gels: Design rationale, recent advances, and perspectives. Chem. Phys. Chem.2014, 15, 2421–2430.
Zhang, X.; Ma, X.; Wang, K.; Lin, S.; Zhu, S.; Dai, Y.; Xia, F. Recent advances in cyclodextrin-based light-responsive supra-molecular systems. Macromol. Rapid Commun.2018, 39, 1800142.
Fox, J. D.; Rowan, S. J. Supramolecular polymerizations and main-chain supramolecular polymers. Macromolecules2009, 42, 6823–6835.
Schoelch, S.; Vapaavuori, J.; Rollet, F. G.; Barrett, C. J. The orange side of disperse red 1: Humidity-driven color switching in supramolecular azo-polymer materials based on reversible dye aggregation. Macromol. Rapid. Commun.2017, 38, 1600582.
Li, Z. Y.; Zhang, Y.; Zhang, C. W.; Chen, L. J.; Wang, C.; Tan, H.; Yu, Y.; Li, X.; Yang, H. B. Cross-linked supra-molecular polymer gels constructed from discrete multi-pillar. J. Am. Chem. Soc.2014, 136, 8577–8589.
Baroncini, M.; Bergamini, G. Azobenzene: A photoactive building block for supramolecular architectures. Chem. Rec.2017, 17, 700–712.
Stoffelen, C.; Voskuhl, J.; Jonkheijm, P.; Huskens, J. Dual stimuli-responsive self-assembled supramolecular nanoparticles. Angew. Chem. Int. Ed.2014, 53, 3400–3404.
Hou, P. P.; Zhang, Z. Y.; Wang, Q.; Zhang, M. Y.; Shen, Z.; Fan, X. H. Hierarchical structures in a main-chain/side-chain combined liquid crystalline polymer with a polynorbornene backbone and multi-benzene side-chain mesogens. Macromolecules2016, 49, 7238–7245.
Chen, H.; Ma, X.; Wu, S.; Tian, H. A rapidly self-healing supramolecular polymer hydrogel with photostimulated room-temperature phosphorescence responsiveness. Angew. Chem. Int Ed.2014, 53, 14149–14152.
Shen, P.; Qiu, L. Dual-responsive recurrent self-assembly of a supramolecular polymer based on the host-guest complexation interaction between β-cyclodextrin and azobenzene. New J. Chem.2018, 42, 3593–3601.
Kuad, P.; Miyawaki, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. External stimulus-responsive supramolecular structures formed by a stilbene cyclodextrin dimer. J. Am. Chem. Soc.2007, 129, 12630–12631.
Zhang, X.; Feng, Y.; Huang, D.; Li, Y.; Feng, W. Investigation of optical modulated conductance effects based on a graphene oxide-azobenzene hybrid. Carbon2010, 48, 3236–3241.
Bortolus, P.; Monti, S. Cis ⇌ trans photoisomerization of azobenzene-cyclodextrin inclusion complexes. J. Phys. Chem.1987, 91, 5046–5050.
Wang, Y.; Ma, N.; Wang, Z.; Zhang, X. Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with α-cyclodextrin. Angew. Chem. Int. Ed.2014, 46, 2823–2826.
Zhang, X.; Feng, Y.; Lv, P.; Shen, Y.; Feng, W. Enhanced reversible photoswitching of azobenzene unctionalized graphene oxide hybrids. Langmuir2010, 26, 18508–18511.
Leenders, C. M.; Albertazzi, L.; Mes, T.; Koenigs, M. M.; Palmans, A. R.; Meijer, E. W. Supramolecular polymerization in water harnessing both hydrophobic effects and hydrogen bond formation. Chem. Commun.2013, 49, 1963–1965.
Nie, J.; Liu, X.; Yan, Y.; Zhang, H. Supramolecular hydrogen-bonded photodriven actuators based on an azobenzene-con-taining main-chain liquid crystalline poly(ester-amide). J. Mater. Chem. C2017, 5, 10391–10398.
Toh, C. L.; Xu, J.; Lu, X.; He, C. Synthesis and characterisation of main-chain hydrogen-bonded supramolecular liquid crystalline complexes formed by azo-containing compounds. Liquid Crystals2008, 35, 241–251.
Rogness, D. C.; Riedel, P. J.; Sommer, J. R.; Reed, D. F.; Wiegel, K. N. Supramolecular main chain liquid crystalline polymers utilizing azopyridine derivatives. Liquid Crystals2006, 33, 567–572.
Sun, R.; Xue, C.; Ma, X.; Gao, M.; Tian, H.; Li, Q. Light-driven linear helical supramolecular polymer formed by molecular-recognition-directed self-assembly of bis(p-sulfon-atocalix[4] arene) and pseudorotaxane. J. Am. Chem. Soc.2013, 135, 5990–5993.
Haque, H. A.; Hara, M.; Nagano, S.; Seki, T. Photoinduced inplane motions of azobenzene mesogens affected by the flexibility of underlying amorphous chains. Macromolecules2013, 46, 8275–8283.
Dai, Y.; Zhang, X. Dual stimuli-responsive supramolecular polymeric nanoparticles based on poly(α-cyclodextrin) and acetal-modified β-cyclodextrin-azobenzene. J. Polym. Res.2018, 25, 102.
Haque, H. A.; Kakehi, S.; Hara, M.; Nagano, S.; Seki, T. High-density liquid-crystalline azobenzene polymer brush attained by surface-initiated ring-opening metathesis polymerization. Langmuir2013, 29, 7571–7575.
Maity, C.; Hendriksen, W. E.; van Esch, J. H.; Eelkema, R. Spatial structuring of a supramolecular hydrogel by using a visible-light triggered catalyst. Angew. Chem. Int. Ed.2015, 54, 998–1001.
Lee, S.; Oh, S.; Lee, J.; Malpani, Y.; Jung, Y. S.; Kang, B.; Lee, J. Y.; Ozasa, K.; Isoshima, T.; Lee, S. Y.; Hara, M.; Hashizume, D.; Hara, M. Stimulus-responsive azobenzene supramolecules: Fibers, gels, and hollow spheres. Langmuir2013, 29, 5869–5877.
Kim, D. Y.; Shin, S.; Yoon, W. J.; Choi, Y. J.; Hwang, J. K.; Kim, J. S.; Lee C. R.; Choi, T. L.; Jeong, K. U. From smart denpols to remote-controllable actuators: Hierarchical superstructures of azobenzene-based polynorbornenes. Adv. Funct. Mater.2017, 27, 1606294.
Fréchet, J. M. Dendrimers and supramolecular chemistry. Proc. Natl. Acad. Sci.2002, 99, 4782–4787.
Qin, C.; Feng, Y.; Luo, W.; Cao, C.; Hu, W.; Feng, W. A supramolecular assembly of cross-linked azobenzene/polymers for a high-performance light-driven actuator. J. Mater. Chem. A2015, 3, 16453–16460.
Li, W.; Zhang, A.; Feldman, K.; Walde, P.; Schlüter, A. D. Thermoresponsive dendronized polymers. Macromolecules2008, 41, 3659–3667.
Roeser, J.; Moingeon, F.; Heinrich, B.; Masson, P.; Arnaud-Neu, F.; Rawiso, M.; Méry, S. Dendronized polymers with peripheral oligo(ethylene oxide) chains: Thermoresponsive behavior and shape anisotropy in solution. Macromolecules2011, 44, 8925–8935.
Liu, L.; Li, W.; Liu, K.; Yan, J.; Hu, G.; Zhang, A. Comblike thermoresponsive polymers with sharp transitions: Synthesis, characterization, and their use as sensitive colorimetric sensors. Macromolecules2011, 44, 8614–8621.
Chivers, P. R.; Smith, D. K. Shaping and structuring supra-molecular gels. Nature Rev. Mater.2019, 1, 463–478.
Yagai, S.; Kitamura, A. Recent advances in photoresponsive supramolecular self-assemblies. Chem. Soc. Rev.2008, 37, 1520–1529.
Stoychev, G.; Kirillova, A.; Ionov, L. Light-responsive shape-changing polymers. Adv. Opt. Mater.2019, 1900067.
Kato, T.; Hirota, N.; Fujishima, A.; Fréchet, J. M. Supra-molecular hydrogen-bonded liquid-crystalline polymer complexes. Design of side-chain polymers and a host-guest system by noncovalent interaction. J. Polym. Sci., Part A: Polym. Chem.1996, 34, 57–62.
Wiedbrauk, S.; Dube, H. Hemithioindigo—An emerging photoswitch. Tetrahedron Lett.2015, 56, 4266–4274.
Yao, X.; Li, T.; Wang, J.; Ma, X.; Tian, H. Recent progress in photoswitchable supramolecular self-assembling systems. Adv. Optical Mater.2016, 4, 1322–1349.
Wang, H.; Zhu, C. N.; Zeng, H.; Ji, X.; Xie, T.; Yan, X.; Wu, Z.; Huang, F. Reversible ion-conducting switch in a novel single-ion supramolecular hydrogel enabled by photoresponsive host-guest molecular recognition. Adv. Mater.2019, 31, 1807328.
Huang, H.; Orlova, T.; Matt, B; Katsonis, N. Long lived supramolecular helices promoted by fluorinated photoswitches. Macromol. Rapid Commun.2018, 39, 1700387.
Ren, H.; Chen, D.; Shi, Y.; Yu, H.; Fu, Z.; Yang, W. Charged end-group terminated poly(N-isopropylacrylamide)-b-poly(carboxylic azo) with unusual thermoresponsive behaviors. Macromolecules2018, 51, 3290–3298.
Yang, C.; Chen, L.; Huang, H.; Lu, Y.; Yi, J. Synthesis and properties of thermo-responsive azobenzene-based supra-molecular dendronized copolymer. Polym. Bull.2018, 1–11.
Si, Q.; Feng, Y.; Yang, W.; Fu, L.; Yan, Q.; Dong, L. P.; Feng, W. Controllable and stable deformation of a self-healing photo-responsive supramolecular assembly for an optically actuated manipulator arm. ACS Appl. Mater. Interface2018, 10, 29909–29917.
Qin, C.; Feng, Y.; An, H.; Han, J.; Cao, C.; Feng, W. Tetracarboxylated azobenzene/polymer supramolecular assemblies as high-performance multiresponsive actuators. ACS Appl. Mater. Interface2017, 9, 4066–4073.
Shen, Y. T.; Deng, K.; Zhang, X. M.; Feng, W.; Zeng, Q. D.; Wang, C.; Gong, J. R. Switchable ternary nanoporous supra-molecular network on photo-regulation. Nano Lett.2011, 11, 3245–3250.
Goodman, M.; Falxa, M. L. Conformational aspects of polypeptide structure. XXIII. Photoisomerization of azoaromatic polypeptides. J. Am. Chem. Soc.1967, 89, 3863–3867.
Yu, H.; Ikeda, T. Photocontrollable liquid-crystalline actuators. Adv. Mater.2011, 23, 2149–2180.
Pawlicka, A.; Sabadini, R. C.; Nunzi, J. M. Reversible light-induced solubility of disperse red 1 dye in a hydroxypropyl cellulose matrix. Cellulose2018, 25, 2083–2090.
Drotlef, D. M.; Amjadi, M.; Yunusa, M.; Sitti, M. Bioinspired composite microfibers for skin adhesion and signal amplification of wearable sensors. Adv. Mater.2017, 29, 1701353.
Feng, Y.; Feng, W. Photo-responsive perylene diimid-azobenzene dyad: Photochemistry and its morphology control by self-assembly. Opt. Mater.2008, 30, 876–880.
Feng, Y.; Feng, W.; Noda, H.; Sekino, T.; Fujii, A.; Ozaki, M.; Yoshino, K. Synthesis of photoresponsive azobenzene chromophore-modified multi-walled carbon nanotubes. Carbon2007, 12, 2445–2448.
Zhao, X.; Feng, Y.; Qin, C.; Yang, W.; Si, Q.; Feng, W. Controlling heat release from a close-packed bisazobenzene-reduced-graphene-oxide assembly film for high-energy solidstate photothermal fuels. ChemSusChem2077, 10, 1395–1404.
Yang, W.; Feng, Y.; Si, Q.; Yan, Q.; Long, P.; Dong, L.; Fu, L.; Feng, W. Efficient cycling utilization of solar-thermal energy for thermochromic displays with controllable heat output. J. Mater. Chem. A2019, 7, 97–106.
Li, M.; Feng, Y.; Liu, E.; Qin, C.; Feng, W. Azobenzene/graphene hybrid for high-density solar thermal storage by optimizing molecular structure. Sci. China Technol. Sci.2016, 59, 1383–1390.
Luo, W.; Feng, Y.; Cao, C.; Li, M.; Liu, E.; Li, S.; Qin, C.; Hu, W.; Feng, W. A high energy density azobenzene/graphene hybrid: A nano-templated platform for solar thermal storage. J. Mater. Chem. A2015, 3, 11787–11795.
Chen, D.; Liu, H.; Kobayashi, T.; Yu, H. Multiresponsive reversible gels based on a carboxylic azo polymer. J. Mater. Chem.2010, 20, 3610–3614.
Ni, Y.; Li, X.; Hu, J.; Huang, S.; Yu, H. Supramolecular liquid-crystalline polymer organogel: Fabrication, multiresponsiveness, and holographic switching properties. Chem. Mater.2019, 31, 3388–3394.
Qin, L.; Gu, W.; Wei, J.; Yu, Y. Piecewise phototuning of self-organized helical superstructures. Adv. Mater.2018, 30, 1704941.
Feng, Y.; Liu, H.; Luo, W.; Liu, E.; Zhao, N.; Yoshino, K.; Feng, W. Covalent functionalization of graphene by azoben-zene with molecular hydrogen bonds for long-term solar thermal storage. Sci. Rep.2013, 3, 3260.
Dong, L.; Feng, Y.; Wang, L.; Feng, W. Azobenzene-based solar thermal fuels: Design, properties, and applications. Chem. Soc. Rev.2018, 47, 7339–7368.
Han, G. G.; Li, H.; Grossman, J. C. Optically-controlled long-term storage and release of thermal energy in phase-change materials. Nat. Commun.2017, 8, 1446.
Kolpak, A. M.; Grossman, J. C. Azobenzene-functionalized carbon nanotubes as high-energy density solar thermal fuels. Nano Lett.2011, 11, 3156–3162.
Kimizuka, N.; Yanai, N.; Morikawa, M. A. Photon upconversion and molecular solar energy storage by maximizing the potential of molecular self-assembly. Langmuir2016, 32, 12304–12322.
Feng, W.; Li, S.; Li, M.; Qin, C.; Feng, Y. An energy-dense and thermal-stable bis-azobenzene/hybrid templated assembly for solar thermal fuel. J. Mater. Chem. A2016, 4, 8020–8028.
Saydjari, A. K.; Weis, P.; Wu, S. Spanning the solar spectrum: Azopolymer solar thermal fuels for simultaneous UV and visible light storage. Adv. Energy Mater.2017, 7, 1601622.
Acknowledgements
This work was financially supported by the National Natural Science Funds for Distinguished Young Scholars (No. 51425306), the National Outstanding Youth Talent Program (2019), the State Key Program of National Natural Science Foundation of China (No. 51633007), the National Natural Science Foundation of China (Nos. 51573125, 51573147, and 51803151), and Scientific and Technological Commission of China.
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Yu, HT., Tang, JW., Feng, YY. et al. Structural Design and Application of Azo-based Supramolecular Polymer Systems. Chin J Polym Sci 37, 1183–1199 (2019). https://doi.org/10.1007/s10118-019-2331-z
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DOI: https://doi.org/10.1007/s10118-019-2331-z