title: Substituent effects on the properties of photochromic hybrid diarylethenes with a naphthalene moiety.
abstract: 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.
authors.affiliation: Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China.
authors.forename: Renjie
authors.initials: R
authors.lastname: Wang
authors.affiliation: Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China.
authors.forename: Xiaorong
authors.initials: X
authors.lastname: Dong
authors.affiliation: Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China. Electronic address: pushouzhi@tsinghua.org.cn.
authors.forename: Shouzhi
authors.initials: S
authors.lastname: Pu
authors.affiliation: Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China.
authors.forename: Gang
authors.initials: G
authors.lastname: Liu
mesh_terms: D002863:Chromogenic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D055664:Electrochemical Techniques; D005030:Ethylenes / Q000138:chemical synthesis / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D007536:Isomerism; D008027:Light; D008958:Models, Molecular; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry*; D055668:Photochemical Processes
chemical_list: D002863:Chromogenic Compounds; D005030:Ethylenes; D005456:Fluorescent Dyes; D009281:Naphthalenes; C031721:naphthalene
keywords: Diarylethene; Naphthalene; Optical and electrochemical property; Photochromism; Substituent effect