Abstract
a series of diarylethene compounds with a thiophene bridging unit have been synthesized to investigate the relationship between molecular structure and photochromic properties. In particular, the fluorescence properties related to compound 1 were investigated. The results showed that a six-membered ring carrying an electron-donating sulfur atom and an electron-withdrawing carbonyl group is necessary to form a “push–pull” system for the fluorescence of 1.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
M. Irie, Diarylethenes for memories and switches, Chem. Rev., 2000, 100, 1685.
G. Jiang, Y. Song, X. Guo, D. Zhang and D. Zhu, Organic Functional Molecules towards Information Processing and High-Density Information Storage, Adv. Mater., 2008, 20, 2888.
R. C. Shallcross, P. Zacharias, A. Köhnen, P. O. Körner, E. Maibach and K. Meerholz, Photochromic Transduction Layers in Organic Memory Elements, Adv. Mater., 2013, 25, 469.
M. Pars, C. C. Hofmann, K. Willinger, P. Bauer, M. Thelakkat and J. Kohler, An organic optical transistor operated under ambient conditions, Angew. Chem., Int. Ed., 2011, 50, 11405.
H. Tian and S. Wang, Photochromic bisthienylethene as multi-function switches, Chem. Commun., 2007, 781.
K. Uchida, Y. Yamanoi, T. Yonezawa and H. Nishihara, Reversible on/off conductance switching of single diarylethene immobilized on a silicon surface, J. Am. Chem. Soc., 2011, 133, 9239.
M. Irie, T. Fukaminato, T. Sasaki, N. Tamai and T. Kawai, A digital fluorescent molecular photoswitch, Nature, 2002, 420, 759.
E. Orgiu, N. r. Crivillers, M. Herder, L. Grubert, M. Pätzel, J. Frisch, E. Pavlica, D. T. Duong, G. Bratina, A. Salleo, N. Koch, S. Hecht, P. Samorí, Optically switchable transistor via energy-level phototuning in a bicomponent organic semiconductor, Nat. Chem., 2012, 4, 675.
W. R. Browne and B. L. Feringa, Making molecular machines work, Nat. Nanotechnol., 2006, 1, 25.
Z. Zhao, Y. Xing, Z. Wang and P. Lu, Dual-Fluorescent Donor–Acceptor Dyad with Tercarbazole Donor and Switchable Imide Acceptor: Promising Structure for an Integrated Logic Gate, Org. Lett., 2007, 9, 547.
J. Folling, V. Belov, R. Kunetsky, R. Medda, A. Schonle, A. Egner, C. Eggeling, M. Bossi and S. W. Hell, Photochromic rhodamines provide nanoscopy with optical sectioning, Angew. Chem., Int. Ed., 2007, 46, 6266.
Y. Kim, H. Y. Jung, Y. H. Choe, C. Lee, S. K. Ko, S. Koun, Y. Choi, B. H. Chung, B. C. Park, T. L. Huh, I. Shin and E. Kim, High-contrast reversible fluorescence photoswitching of dye-crosslinked dendritic nanoclusters in living vertebrates, Angew. Chem., Int. Ed., 2012, 51, 2878.
W. Tan, J. Zhou, F. Li, T. Yi and H. Tian, Visible light-triggered photoswitchable diarylethene-based iridium(III) complexes for imaging living cells, Chem.–Asian J., 2011, 6, 1263.
N. Soh, K. Yoshida, H. Nakajima, K. Nakano, T. Imato, T. Fukaminato and M. Irie, A fluorescent photochromic compound for labeling biomolecules, Chem. Commun., 2007, 5206.
D. Hu, Z. Tian, W. Wu, W. Wan and A. D. Q. Li, Photoswitchable Nanoparticles Enable High-Resolution Cell Imaging: PULSAR Microscopy, J. Am. Chem. Soc., 2008, 130, 15279.
Z. Tian, W. Wu, W. Wan and A. D. Li, Photoswitching-induced frequency-locked donor-acceptor fluorescence double modulations identify the target analyte in complex environments, J. Am. Chem. Soc., 2011, 133, 16092.
I. Yildiz, S. Impellizzeri, E. Deniz, B. McCaughan, J. F. Callan and F. M. Raymo, Supramolecular strategies to construct biocompatible and photoswitchable fluorescent assemblies, J. Am. Chem. Soc., 2011, 133, 871.
T. Y. Ying Zou, S. Xiao, F. Li, C. Li, X. Gao, J. Wu, M. Yu and C. Huang, Amphiphilic Diarylethene as a Photoswitchable Probe for Imaging Living Cells, J. Am. Chem. Soc., 2008, 130, 15750.
U. Al-Atar, R. Fernandes, B. Johnsen, D. Baillie and N. R. Branda, A Photocontrolled Molecular Switch Regulates Paralysis in a Living Organism, J. Am. Chem. Soc., 2009, 131, 15966.
X. Piao, Y. Zou, J. Wu, C. Li and T. Yi, Multiresponsive Switchable Diarylethene and Its Application in Bioimaging, Org. Lett., 2009, 11, 3818.
J. Folling, S. Polyakova, V. Belov, A. van Blaaderen, M. L. Bossi and S. W. Hell, Synthesis and characterization of photoswitchable fluorescent silica nanoparticles, Small, 2008, 4, 134.
H. Y. Jung, S. You, C. Lee and Y. Kim, One-pot synthesis of monodispersed silica nanoparticles for diarylethene-based reversible fluorescence photoswitching in living cells, Chem. Commun., 2013, 49, 7528.
T. Yang, Q. Liu, J. Li, S. Pu, P. Yang and F. Li, Photoswitchable upconversion nanophosphors for small animal imaging in vivo, RSC Adv., 2014, 4, 15613.
K. Liu, Y. Wen, T. Shi, Y. Li, F. Li, Y. L. Zhao, C. Huang and T. Yi, DNA gated photochromism and fluorescent switch in a thiazole orange modified diarylethene, Chem. Commun., 2014, 50, 9141.
J. Zhang, Q. Zou and H. Tian, Photochromic materials: more than meets the eye, Adv. Mater., 2013, 25, 378.
T. Fukaminato, Single-molecule fluorescence photoswitching: Design and synthesis of photoswitchable fluorescent molecules, J. Photochem. Photobiol., C, 2011, 12, 177.
M. Bossi, V. Belov, S. Polyakova and S. W. Hell, Reversible red fluorescent molecular switches, Angew. Chem., Int. Ed., 2006, 45, 7462.
T. Fukaminato, T. Doi, N. Tamaoki, K. Okuno, Y. Ishibashi, H. Miyasaka and M. Irie, Single-molecule fluorescence photoswitching of a diarylethene-perylenebisimide dyad: non-destructive fluorescence readout, J. Am. Chem. Soc., 2011, 133, 4984.
L. Giordano, T. M. Jovin, M. Irie, E. A. Jares-Erijman, Diheteroarylethenes as Thermally Stable Photoswitchable Acceptors in Photochromic Fluorescence Resonance Energy Transfer (pcFRET), J. Am. Chem. Soc., 2002, 124, 7481.
K. Ouhenia-Ouadahi, R. Metivier, S. Maisonneuve, A. Jacquart, J. Xie, A. Leaustic, P. Yu and K. Nakatani, Fluorescence photoswitching and photoreversible two-way energy transfer in a photochrome-fluorophore dyad, Photochem. Photobiol. Sci., 2012, 11, 1705.
S. Pu, H. Ding, G. Liu, C. Zheng and H. Xu, Multiaddressing Fluorescence Switch Based on a New Photochromic Diarylethene with a Triazole-Linked Rhodamine B Unit, J. Phys. Chem. C, 2014, 118, 7010.
C. Li, W.-L. Gong, Z. Hu, M. P. Aldred, G.-F. Zhang, T. Chen, Z.-L. Huang, M.-Q. Zhu, Photoswitchable aggregation-induced emission of a dithienylethene–tetraphenylethene conjugate for optical memory and super-resolution imaging, RSC Adv., 2013, 3, 8967.
S. Pu, L. Ma, G. Liu, H. Ding and B. Chen, A multiple switching diarylethene with a phenyl-linked rhodamine B unit and its application as chemosensor for Cu2+, Dyes Pigm., 2015, 113, 70.
Y. C. Jeong, S. I. Yang, K. H. Ahn and E. Kim, Highly fluorescent photochromic diarylethene in the closed-ring form, Chem. Commun., 2005, 2503.
S.-C. Pang, H. Hyun, S. Lee, D. Jang, M. J. Lee, S. H. Kang, K.-H. Ahn, Photoswitchable fluorescent diarylethene in a turn-on mode for live cell imaging, Chem. Commun., 2012, 48, 3745.
Z. Li, J. Xia, J. Liang, J. Yuan, G. Jin, J. Yin, G.-A. Yu and S. H. Liu, Synthesis of diarylethene derivatives containing various heterocycles and tuning of light-emitting properties in a turn-on fluorescent diarylethene system, Dyes Pigm., 2011, 90, 290.
K. Uno, H. Niikura, M. Morimoto, Y. Ishibashi, H. Miyasaka and M. Irie, In situ preparation of highly fluorescent dyes upon photoirradiation, J. Am. Chem. Soc., 2011, 133, 13558.
H.-h. Liu and Y. Chen, The Photochromism and Fluorescence of Diarylethenes with a Imidazole Bridge Unit: A Strategy for the Design of Turn-on Fluorescent Diarylethene System, J. Phys. Chem. A, 2009, 113, 5550.
Y.-C. Jeong, D. G. Park, I. S. Lee, S. I. Yang, K.-H. Ahn, Highly fluorescent photochromic diarylethene with an excellent fatigue property, J. Mater. Chem., 2009, 19, 97.
Y.-C. Jeong, J. P. Han, Y. Kim, E. Kim, S. I. Yang, K.-H. Ahn, Characterization and photophysical properties of sulfur-oxidized diarylethenes, Tetrahedron, 2007, 63, 3173.
Y.-C. Jeong, S. I. Yang, E. Kim, K.-H. Ahn, Development of highly fluorescent photochromic material with high fatigue resistance, Tetrahedron, 2006, 62, 5855.
M. Taguchi, T. Nakagawa, T. Nakashima and T. Kawai, Photochromic and fluorescence switching properties of oxidized triangle terarylenes in solution and in amorphous solid states, J. Mater. Chem., 2011, 21, 17425.
M. Taguchi, T. Nakagawa, T. Nakashima, C. Adachi and T. Kawai, Photo-patternable electroluminescence based on one-way photoisomerization reaction of tetraoxidized triangle terarylenes, Chem. Commun., 2013, 49, 6373.
B. Huang, Super-resolution optical microscopy: multiple choices, Curr. Opin. Chem. Biol., 2010, 14, 10.
S. W. Hell, Microscopy and its focal switch, Nat. Methods, 2009, 6, 24.
S. W. Hell, R. Schmidt and A. Egner, Diffraction-unlimited three-dimensional optical nanoscopy with opposing lenses, Nat. Photonics, 2009, 3, 381.
X. Zhuang, Nano-imaging with STORM, Nat. Photonics, 2009, 3, 365.
M. Bates, B. Huang, G. T. Dempsey and X. Zhuang, Multicolor Super-Resolution Imaging with Photo-Switchable Fluorescent Probes, Science, 2007, 317, 1749.
T. J. Blacklock, P. Sohar, J. W. Butcher, T. Lamanec and E. J. J. Grabowski, An Enantioselective Synthesis of the Topically-Active Carbonic Anhydrase Inhibitor MK-0507: 5,6-Dihydro-(S)-(ethylamino)-(S)-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-Dioxide Hydrochloride, J. Org. Chem., 1993, 58, 1672.
S. Delbaere and G. Vermeersch, NMR spectroscopy applied to photochromism investigations, J. Photochem. Photobiol., C, 2008, 9, 61.
K. Matsuda and M. Irie, A Diarylethene with Two Nitronyl Nitroxides: Photoswitching of Intramolecular Magnetic Interaction, J. Am. Chem. Soc., 2000, 122, 7195.
Y. Ishibashi, M. Fujiwara, T. Umesato, H. Saito, S. Kobatake, M. Irie and H. Miyasaka, Cyclization Reaction Dynamics of a Photochromic Diarylethene Derivative as Revealed by Femtosecond to Microsecond Time-Resolved Spectroscopy, J. Phys. Chem. C, 2011, 115, 4265.
A. Staykov and K. Yoshizawa, Photochemical Reversibility of Ring-Closing and Ring-Opening Reactions in Diarylperfluorocyclopentene, J. Phys. Chem. C, 2009, 113, 3826.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Pang, S., Jang, D., Lee, W.S. et al. The effect of a “push—pull” structure on the turn-on fluorescence of photochromic thio-ketone type diarylethenes. Photochem Photobiol Sci 14, 765–774 (2015). https://doi.org/10.1039/c4pp00320a
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c4pp00320a