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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2012
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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. |
format | Online Article Text |
id | pubmed-3458719 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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