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The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety

Three new isomeric asymmetric diarylethenes with a naphthyl moiety and a formyl group at the para, meta or ortho position of the terminal benzene ring were synthesized. Their photochromism, fluorescent-switch, and electrochemical properties were investigated. Among these diarylethenes, the one with...

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Autores principales: Wang, Renjie, Pu, Shouzhi, Liu, Gang, Cui, Shiqiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458719/
https://www.ncbi.nlm.nih.gov/pubmed/23019429
http://dx.doi.org/10.3762/bjoc.8.114
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author Wang, Renjie
Pu, Shouzhi
Liu, Gang
Cui, Shiqiang
author_facet Wang, Renjie
Pu, Shouzhi
Liu, Gang
Cui, Shiqiang
author_sort Wang, Renjie
collection PubMed
description Three new isomeric asymmetric diarylethenes with a naphthyl moiety and a formyl group at the para, meta or ortho position of the terminal benzene ring were synthesized. Their photochromism, fluorescent-switch, and electrochemical properties were investigated. Among these diarylethenes, the one with a formyl group at the ortho position of benzene displayed the largest molar absorption coefficients and fluorescence quantum yield. The cyclization quantum yields of these compounds increased in the order of para < ortho < meta, whereas their cycloreversion quantum yields decreased in the order of meta > para > ortho. Additionally, all of these diarylethenes functioned as effective fluorescent switches in both solution and PMMA films. Cyclic voltammograms proved that the formyl group and its position could effectively modulate the electrochemical behaviors of these diarylethene derivatives.
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spelling pubmed-34587192012-09-27 The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety Wang, Renjie Pu, Shouzhi Liu, Gang Cui, Shiqiang Beilstein J Org Chem Full Research Paper Three new isomeric asymmetric diarylethenes with a naphthyl moiety and a formyl group at the para, meta or ortho position of the terminal benzene ring were synthesized. Their photochromism, fluorescent-switch, and electrochemical properties were investigated. Among these diarylethenes, the one with a formyl group at the ortho position of benzene displayed the largest molar absorption coefficients and fluorescence quantum yield. The cyclization quantum yields of these compounds increased in the order of para < ortho < meta, whereas their cycloreversion quantum yields decreased in the order of meta > para > ortho. Additionally, all of these diarylethenes functioned as effective fluorescent switches in both solution and PMMA films. Cyclic voltammograms proved that the formyl group and its position could effectively modulate the electrochemical behaviors of these diarylethene derivatives. Beilstein-Institut 2012-07-05 /pmc/articles/PMC3458719/ /pubmed/23019429 http://dx.doi.org/10.3762/bjoc.8.114 Text en Copyright © 2012, Wang et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Wang, Renjie
Pu, Shouzhi
Liu, Gang
Cui, Shiqiang
The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety
title The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety
title_full The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety
title_fullStr The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety
title_full_unstemmed The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety
title_short The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety
title_sort effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458719/
https://www.ncbi.nlm.nih.gov/pubmed/23019429
http://dx.doi.org/10.3762/bjoc.8.114
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