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Substituent position effect on the properties of isomeric photochromic diarylethenes bearing chlorine atoms

Paper ID Volume ID Publish Year Pages File Format Full-Text
29177 44127 2008 11 PDF Available
Title
Substituent position effect on the properties of isomeric photochromic diarylethenes bearing chlorine atoms
Abstract

Three new isomeric photochromic diarylethenes, namely 1,2-bis[2-methyl-5-(4-chlorophenyl)-3-thienyl]perfluorocyclopentene (1o), 1,2-bis[2-methyl-5-(3-chlorophenyl)-3-thienyl]perfluorocyclopentene (2o), and 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]perfluorocyclopentene (3o) which bear two chlorine atoms at the para-, meta-, and ortho-position of both terminal phenyl groups, have been synthesized. The substituent position effect of chlorine atoms on their optoelectronic properties, including photochromic behavior and fluorescence, both in solution and in PMMA amorphous film, and electrochemical properties were investigated in detail. The results elucidated that the chlorine atoms and their substituent positions had a significant effect on the optoelectronic properties of these compounds. These diarylethene derivatives bearing two chlorine atoms have shown good photochromic behavior and fluorescent switching both in solution and in PMMA film. For diarylethenes 1–3, the cycloreversion quantum yields were gradually increased when the chlorine atom was attached to the para-, meta- and ortho-positions of the two terminal benzene rings; but, their absorption maxima, cyclization quantum yields and the molar absorption coefficients both of their open-ring and closed-ring isomers were remarkably decreased one by one. Furthermore, the clear oxidation waves of diarylethenes 1c, 2c and 3c were observed at 1.01, 0.92 and 0.98 V by performing the cyclic voltammograms experiments.

Keywords
Photochromism; Diarylethene; Chlorine atom position effect; Optoelectronic property
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Substituent position effect on the properties of isomeric photochromic diarylethenes bearing chlorine atoms
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 194, Issues 2–3, 20 February 2008, Pages 333–343
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
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Any Questions? feel free to contact us