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Photophysical studies of substituted 1,2-diarylethenes: twisted intramolecular charge transfer fluorescence in dimethoxycyano-substituted 1,2-diarylethene

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Title Photophysical studies of substituted 1,2-diarylethenes: twisted intramolecular charge transfer fluorescence in dimethoxycyano-substituted 1,2-diarylethene
 
Creator SINGH, AK
KANVAH, S
 
Subject dual fluorescence
pi-star
photoisomerization
stilbenes
systems
states
 
Description 1,2-Diarylethenes, namely (E)-1-(4-cyanophenyl)-2-phenylethene (1), (E)-1-(4-methoxyphenyl)-2-phenylethene (2), (E)-1-(3,4-dimethoxyphenyl)-2-phenylethene (3), (E)-1-(4-cyanophenyl)-2-(4-methoxyphenyl)ethene (4) and (E)-1-(4-cyanophenyl)-2-(3,4-dimethoxyphenyl)ethene (5), have been synthesized and their absorption and fluorescence properties at room temperature in different organic solvents and also in 1,4-dioxane-water binary mixtures have been investigated. Additionally, the fluorescence of these compounds has been examined at 77 K in an ethanol-methanol (1:1 v/v) matrix. Photophysical parameters like absorption, excitation and fluorescence spectra, fluorescence quantum yields, excited state dipole moment changes, and correlation of solvatochromic fluorescence with solvent parameters like E-T(30)-values and the pi*-scale have been made. Compound 5, with one cyano and two methoxy substituents, has been found to exhibit solvent polarity-dependent dual fluorescence. The shorter wavelength fluorescence is attributed to an initially excited delocalized planar state, while the longer wavelength fluorescence is attributed to a non-planar twisted intramolecular charge transfer excited state.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2011-08-28T15:44:23Z
2011-12-26T12:58:06Z
2011-12-27T05:47:23Z
2011-08-28T15:44:23Z
2011-12-26T12:58:06Z
2011-12-27T05:47:23Z
2001
 
Type Article
 
Identifier JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, (3), 395-401
1472-779X
http://dx.doi.org/10.1039/b006657p
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11777
http://hdl.handle.net/10054/11777
 
Language en