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Issue 3, 2001
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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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Abstract

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 ET(30)-values and the π*-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.

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

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Article information


Submitted
15 Aug 2000
Accepted
16 Nov 2000
First published
06 Feb 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 395-401
Article type
Paper

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

A. K. Singh and S. Kanvah, J. Chem. Soc., Perkin Trans. 2, 2001, 395
DOI: 10.1039/B006657P

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