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Photochromism of new unsymmetrical diarylethenes with a quinoline moiety
Author(s) -
Liu Peng,
Liu Hongliang,
Liu Gang,
Zhang Zhihui,
Xu Fen,
Pu Shouzhi
Publication year - 2017
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3716
Subject(s) - photoisomerization , diarylethene , photochromism , moiety , chemistry , quinoline , photochemistry , trifluoromethyl , aryl , ring (chemistry) , alkyl , isomerization , stereochemistry , organic chemistry , catalysis
Abstract Three unsymmetrical diarylethenes with a 6‐membered quinoline moiety were synthesized to investigate the effects of the substituents on their photochromism, and fluorescence, and the structure of one diarylethene was determined by single crystal X‐ray diffraction analysis. Quinoline was connected directly to the central perfluorocyclopentene ring as an aryl moiety and available to participate in photoisomerization reaction in solution, amorphous films, and crystalline phase. These diarylethenes exhibited good photochromism with excellent thermal stability and obvious fatigue resistance. The electron‐donating methoxy group could enhance the absorption maxima of closed‐ring isomers and the quantum yields of cyclization and cycloreversion, but the electron‐withdrawing trifluoromethyl had an opposite effect. In addition, they functioned as notable fluorescence switches in both solution and polymethylmethacrylate films, and the trifluoromethyl group and the methoxy group both increased the emission intensity. The results revealed that the quinoline moiety and substituents played a vital role in the process of photoisomerization reactions for these diarylethenes.