Synthesis and Properties of Photochromic Dithienylethene Compounds with Triphenylamine Units

doi:10.6023/A14030158

Acta Chimica Sinica ›› 2014, Vol. 72 ›› Issue (6): 731-738.DOI: 10.6023/A14030158 Previous Articles Next Articles

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含三苯胺基团的二噻吩乙烯光致变色化合物的合成及性能研究

王志强^a,b, 肖殷^a,b, 金会义^a,b, 谈廷风^c, 王世荣^a,b, 李祥高^a,b

a. 天津大学化工学院天津 300072;
b. 天津化学化工协同创新中心天津 300072;
c. 天津城建大学理学院天津 300384

投稿日期:2014-03-07 发布日期:2014-05-14
通讯作者: 李祥高 E-mail:lixianggao@tju.edu.cn
基金资助:
项目受国家自然科学基金（No.21102098）和国家高技术研究发展计划（863计划，No.2012AA030307）资助.

Synthesis and Properties of Photochromic Dithienylethene Compounds with Triphenylamine Units

Wang Zhiqiang^a,b, Xiao Yin^a,b, Jin Huiyi^a,b, Tan Tingfeng^c, Wang Shirong^a,b, Li Xianggao^a,b

a. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072;
b. The Co-Innovation Center of Chemistry and Chemical Engineering of Tianjin, Tianjin 300072;
c. School of Science, Tianjin Chengjian University, Tianjin 300384

Received:2014-03-07 Published:2014-05-14
Supported by:
Project supported by the National Natural Science Foundation of China (No.21102098) and the National High Technology Research and Development Program of China (863 Program, No.2012AA030307).

1. Synthesis and Properties of Photochromic Dithienylethene Compounds with Triphenylamine Units.PDF(1374KB)

Abstract

Combining dithienylethene photochromic unit with triphenylamine unit, three new photochromic dithienylethene compounds 1a～1c were successfully synthesized using 5-chloro-2-methyl-3-acetylthiophene and diphenylaminobenzaldehydes as starting materials through Aldol condensation reaction, Michael addition reaction and McMurry coupling reaction, the structures of which were characterized by MS, ¹H NMR and ¹³C NMR.Different from majority of previous studies that introduce different functional groups through thiophene rings, we bridged the triphenylamine unit with fluorescence property to the cyclopentene at β-position via C—C single bond, which will maintain the activation of photochromism and prevent other functional groups affecting the dithienylethene backbone.Their photochromic and fluorescence properties in solutions and polymethylmethacrylate films were investigated by UV-Vis and fluorescence spectra, respectively.The colorless solutions and films of 1a～1c switch to yellow upon irradiation with 302 nm UV light and reach the photostationary state fast, while bleaching of the colored solutions happen upon irradiation with 450 nm blue light.When 1a～1c are excited by UV light, the maximum fluorescence wavelengths of 1a～1c increase along with the enhancement of the abilities of electron donating of substituent R, and 1a～1c emit strong fluorescence in n-hexane, toluene and ethyl acetate, while weak in acetonitrile and none in chloroform.Moreover, upon irradiation at 302 nm, Förster resonance energy transfer occurs between triphenylamine unit and dithienylcyclopentene unit of 1a～1c.Thus, the fluorescence intensities of 1a～1c decrease along with the prolonging of irradiation time, which indicates the potential application of these compounds as fluorescence molecular switches.

Key words: dithienylethene, triphenylamine, photochromic, fluorescence molecular switch, Förster resonance energy transfer

Cite this article

Wang Zhiqiang, Xiao Yin, Jin Huiyi, Tan Tingfeng, Wang Shirong, Li Xianggao. Synthesis and Properties of Photochromic Dithienylethene Compounds with Triphenylamine Units[J]. Acta Chimica Sinica, 2014, 72(6): 731-738.

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含三苯胺基团的二噻吩乙烯光致变色化合物的合成及性能研究

Synthesis and Properties of Photochromic Dithienylethene Compounds with Triphenylamine Units

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