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Pure Appl. Chem., 1996, Vol. 68, No. 7, pp. 1367-1371

http://dx.doi.org/10.1351/pac199668071367

Photochromic diarylethenes for photonic devices

M. Irie

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  • Sun Zhiyuan, Li Hui, Liu Gang, Fan Congbin, Pu Shouzhi: Photochromism of new unsymmetrical diarylethenes based on the hybrid of azaindole and thiophene moieties. Dyes and Pigments 2014, 106, 94. <http://dx.doi.org/10.1016/j.dyepig.2014.03.003>
  • Sun Zhiyuan, Li Hui, Pu Shouzhi, Liu Gang, Chen Bing: Synthesis and photochromism of novel unsymmetrical diarylethenes with an azaindole unit. Tetrahedron Letters 2014, 55, 2471. <http://dx.doi.org/10.1016/j.tetlet.2014.03.004>
  • Zheng Chunhong, Pu Shouzhi, Pang Zhiyi, Chen Bing, Liu Gang, Dai Yanfeng: Syntheses and photochromism of new isomeric diarylethenes bearing an indole moiety. Dyes and Pigments 2013, 98, 565. <http://dx.doi.org/10.1016/j.dyepig.2013.04.003>
  • Nakagawa Hisako, Nakashima Takuya, Kawai Tsuyoshi: Subsequent Chemical Reactions of Photochromic 4,5-Dibenzothienylthiazoles. Eur. J. Org. Chem. 2012, 2012, 4493. <http://dx.doi.org/10.1002/ejoc.201200465>
  • Shirinian Valerii Z., Shimkin Alexey A., Lonshakov Dmitry V., Lvov Andrey G., Krayushkin Mikhail M.: Synthesis and spectral properties of a novel family of photochromic diarylethenes-2,3-diarylcyclopent-2-en-1-ones. Journal of Photochemistry and Photobiology A: Chemistry 2012, 233, 1. <http://dx.doi.org/10.1016/j.jphotochem.2012.02.011>
  • Dong Huanli, Zhu Hongfei, Meng Qing, Gong Xiong, Hu Wenping: Organic photoresponse materials and devices. Chemical Society Review 2012, 41, 1754. <http://dx.doi.org/10.1039/c1cs15205j>
  • Cipolloni Marco, Heynderickx Arnault, Maurel François, Perrier Aurélie, Jacquemin Denis, Siri Olivier, Ortica Fausto, Favaro Gianna: Multiswitchable Acidichromic and Photochromic Bisdiarylethene. An Experimental and Theoretical Study. J. Phys. Chem. C 2011, 115, 23096. <http://dx.doi.org/10.1021/jp205681p>
  • Marinotto Daniele, Castagna Rossella, Righetto Stefania, Dragonetti Claudia, Colombo Alessia, Bertarelli Chiara, Garbugli Michele, Lanzani Guglielmo: Photoswitching of the Second Harmonic Generation from Poled Phenyl-Substituted Dithienylethene Thin Films and EFISH Measurements. J Phys Chem C 2011, 115, 20425. <http://dx.doi.org/10.1021/jp2060409>
  • Rode Michał F., Sobolewski Andrzej L.: Effect of Chemical Substituents on the Energetical Landscape of a Molecular Photoswitch: An Ab Initio Study. J Phys Chem A 2010, 114, 11879. <http://dx.doi.org/10.1021/jp105710n>
  • di Nunzio Maria Rosaria, Danilov Evgeny O., Rodgers Michael A. J., Favaro Gianna: Ultrafast excited-state dynamics in some spirooxazines and chromenes. Evidence for a dual relaxation pathway. Photochem Photobiol Sci 2010, 9, 1391. <http://dx.doi.org/10.1039/c0pp00149j>
  • Cipolloni M., Ortica F., El Yahyaoui A., Heynderickx A., Moustrou C., Favaro G.: New photochromic symmetrical and unsymmetrical bis(heteroaryl)maleimides: A spectrokinetic study. Chemical Phys 2009, 358, 258. <http://dx.doi.org/10.1016/j.chemphys.2009.02.011>
  • Hermes Stephan, Dassa Giovanni, Toso Giorgio, Bianco Andrea, Bertarelli Chiara, Zerbi Giuseppe: New fast synthesis route for symmetric and asymmetric phenyl-substituted photochromic dithienylethenes bearing functional groups such as alcohols, carboxylic acids, or amines. Tetrahetron Lett 2009, 50, 1614. <http://dx.doi.org/10.1016/j.tetlet.2009.01.102>
  • Bougdid Lahoussine, Samat Andre, Moustrou Corinne: New photochromic diarylethenes including P and Si atoms. New J Chem 2009, 33, 1357. <http://dx.doi.org/10.1039/b901277j>
  • Santos André Ribeiro, Ballardini Roberto, Belser Peter, Gandolfi Maria Teresa, Iyer Vijay Mahadevan, Moggi Luca: Photochemical investigation of a photochromic diarylethene compound that can be used as a wide range actinometer. Photochem Photobiol Sci 2009, 8, 1734. <http://dx.doi.org/10.1039/b9pp00037b>
  • Nigel Corns S, Partington Steven M, Towns Andrew D: Industrial organic photochromic dyes : Industrial organic photochromic dyes. Coloration Technol 2009, 125, 249. <http://dx.doi.org/10.1111/j.1478-4408.2009.00204.x>
  • Moulton Benjamin E., Dong Hao, O'Brien Ciara T., Duckett Simon B., Lin Zhenyang, Fairlamb Ian J. S.: A natural light induced regioselective 6π-electrocyclisation–oxidative aromatisation reaction: experimental and theoretical insights. Org Biomol Chem 2008, 6, 4523. <http://dx.doi.org/10.1039/b811284c>
  • Kay Euan R., Leigh David A., Zerbetto Francesco: Synthetische molekulare Motoren und mechanische Maschinen. Angew Chem 2007, 119, 72. <http://dx.doi.org/10.1002/ange.200504313>
  • Kay Euan R., Leigh David A., Zerbetto Francesco: Synthetic Molecular Motors and Mechanical Machines. Angew Chem Int Ed 2007, 46, 72. <http://dx.doi.org/10.1002/anie.200504313>
  • Kamrul Hossain Mohammed, Takeshita Michinori, Yamato Takehiko: Synthesis, Structure, and Photochromic Properties of Dithia-(dithienylethena)phane Derivatives. Eur J Org Chem 2005, 2005, 2771. <http://dx.doi.org/10.1002/ejoc.200400807>
  • Shin Hee-Won, Kim Yong-Rok, Kim Eunkyoung: Photochromic polysiloxanes substituted with 1,2-Bis(2-methylbenzo[b]thiophene-3-yl)hexafluorocyclopentene. Macromol Res 2005, 13, 321. <http://dx.doi.org/10.1007/BF03218460>
  • Hossain Mohammed Kamrul, Takeshita Michinori, Yamato Takehiko: Synthesis and photochromic properties of a dithia-dithienylethenophane. Tetrahetron Lett 2005, 46, 431. <http://dx.doi.org/10.1016/j.tetlet.2004.11.090>
  • Miyasaka Hiroshi, Murakami Masataka, Okada Tadashi, Nagata Yasushi, Itaya Akira, Kobatake Seiya, Irie Masahiro: Picosecond and femtosecond laser photolysis studies of a photochromic diarylethene derivative: multiphoton gated reaction. chem phys letts 2003, 371, 40. <http://dx.doi.org/10.1016/S0009-2614(03)00219-7>
  • Saito M., Honda A., Uchida K.: Photochromic liquid-core fibers with nonlinear input~output characteristics. J Lightwave Technol 2003, 21, 2255. <http://dx.doi.org/10.1109/JLT.2003.817703>
  • Mrozek Thomas, Görner Helmut, Daub Jörg: Multimode-Photochromism Based on Strongly Coupled Dihydroazulene and Diarylethene. Chem Eur J 2001, 7, 1028. <http://dx.doi.org/10.1002/1521-3765(20010302)7:5<1028::AID-CHEM1028>3.0.CO;2-7>
  • Kwon Doo-Hyung, Shin Hee-Won, Kim Eunkyoung, Boo Doo Wan, Kim Yong-Rok: Photochromism of diarylethene derivatives in rigid polymer matrix: structural dependence, matrix effect, and kinetics. chem phys letts 2000, 328, 234. <http://dx.doi.org/10.1016/S0009-2614(00)00893-9>
  • Kuldová K, Tsyganenko K, Corval A, Trommsdorff H.P, Bens A.T, Kryschi C: Photo-switchable dithienylethenes: threshold of the photoreactivity. Synthetic Metal 2000, 115, 163. <http://dx.doi.org/10.1016/S0379-6779(00)00327-1>
  • Port H., Hartschuh A., Hennrich M., Wolf H. C., Endtner J. M., Effenberger F.: Photoswitching Intramolecular Energy and Charge Transfer. Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals 2000, 344, 145. <http://dx.doi.org/10.1080/10587250008023828>
  • Kasatani Kazuo, Kambe Shingo, Irie Masahiro: Photochromic Reaction and Fluorescence of Dithienylethenes in Solid States. Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals 2000, 345, 45. <http://dx.doi.org/10.1080/10587250008023893>
  • Higashiguchi Kenji, Matsuda Kenji, Kobatake Seiya, Yamada Taro, Kawai Tsuyoshi, Irie Masahiro: Fatigue Mechanism of Photochromic 1,2-Bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene. Bull Chem Soc Jpn 2000, 73, 2389. <http://dx.doi.org/10.1246/bcsj.73.2389>
  • Kawai Stephen H., Gilat Sylvain L., Lehn Jean-Marie: Photochemical pKa-Modulation and Gated Photochromic Properties of a Novel Diarylethene Switch. Eur J Org Chem 1999, 1999, 2359. <http://dx.doi.org/10.1002/(SICI)1099-0690(199909)1999:9<2359::AID-EJOC2359>3.0.CO;2-#>
  • Takeshita Michinori, Irie Masahiro: Photoreversible circular dichroism change of 1,2-bis(1-benzothiophen-3-yl)perfluorocyclopentene modified cyclodextrin. Tetrahetron Lett 1999, 40, 1345. <http://dx.doi.org/10.1016/S0040-4039(98)02658-6>
  • Kasatani Kazuo, Kambe Shingo, Irie Masahiro: Photochromic reaction and fluorescence of dithienylethenes in the solid state. J Photochem Photobiol A Chem 1999, 122, 11. <http://dx.doi.org/10.1016/S1010-6030(99)00016-7>
  • A Light Induced Change in Cholesteric Pitch by Photoracemization of a Chiral Pyrenyl Sulfoxide. Chem Lett 1999, 87. <http://dx.doi.org/10.1246/cl.1999.87>
  • Uchida Kingo, Ishikawa Takayuki, Takeshita Michinori, Irie Masahiro: Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-bis(thiazolyl)perfluorocyclopentenes. Tetrahedron 1998, 54, 6627. <http://dx.doi.org/10.1016/S0040-4020(98)00330-5>
  • Takeshita Michinori, Soong Chai Fong, Irie Masahiro: Alkali metal ion effect on the photochromism of 1,2-bis(2,4-dimethylthien-3-yl)-perfluorocyclopentene having benzo-15-crown-5 moieties. Tetrahetron Lett 1998, 39, 7717. <http://dx.doi.org/10.1016/S0040-4039(98)01681-5>
  • Irie Masahiro, Uchida Kingo: Synthesis and Properties of Photochromic Diarylethenes with Heterocyclic Aryl Groups. Bull Chem Soc Jpn 1998, 71, 985. <http://dx.doi.org/10.1246/bcsj.71.985>
  • Miyasaka Hiroshi, Nobuto Takahiro, Itaya Akira, Tamai Naoto, Irie Masahiro: Picosecond laser photolysis studies on a photochromic dithienylethene in solution and in crystalline phases. chem phys letts 1997, 269, 281. <http://dx.doi.org/10.1016/S0009-2614(97)00282-0>
  • Asahi Tsuyoshi, Masuhara Hiroshi: Photocoloration of Spironaphthoxazine Microcrystalline Powder by Femtosecond Laser Pulse Excitation. Chem Lett 1997, 1165. <http://dx.doi.org/10.1246/cl.1997.1165>