US EPA

2708654 

Journal Article 

Substituent effects on the properties of photochromic hybrid diarylethenes with a naphthalene moiety 

Wang, R; Dong, X; Pu, S; Liu, G 

2015 

1 

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
ISSN: 1386-1425
EISSN: 1873-3557 

137 

1222-1230 

English 

25305614 

10.1016/j.saa.2014.09.022 

WOS:000347269900148 

http://://WOS:000347269900148
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Four new unsymmetrical photochromic diarylethenes bearing both naphthalene and thiophene moieties were synthesized, and the structures of two diarylethenes were determined by single-crystal X-ray diffraction analysis. The naphthalene ring was connected directly to the central perfluorocyclopentene ring as an aryl moiety and available to participate in photoisomerization reaction. All the diarylethenes exhibited favorable photochromism and functioned as fluorescence switches in both solution and poly(methyl methacrylate) films. The electron-withdrawing substituent significantly shifted the absorption maxima to a longer wavelength and evidently suppressed the cycloreversion quantum yield, whereas the electron-donating substituents enhanced the fluorescence quantum yield of diarylethenes with a naphthalene moiety. Furthermore, cyclic voltammograms suggested that the oxidation onsets and band-gaps of the open-ring isomers were much bigger than those of the closed-ring isomers. The results indicated that the substituents at the 5-position of thiophene ring could availably modulate their optical and electrochemical behaviors. 

Chromogenic Compounds/chemical synthesis/chemistry; Crystallography, X-Ray; Electrochemical Techniques; Ethylenes/chemical synthesis/chemistry; Fluorescent Dyes/chemical synthesis/chemistry; Isomerism; Models, Molecular; Naphthalenes/chemical synthesis/chemistry; Photochemical Processes; Diarylethene; Naphthalene; Optical and electrochemical property; Photochromism; Substituent effect