meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical properties

meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical properties

The investigation of multi-photochromic compounds constitutes a great challenge, not only from a synthetic point of view, but also with respect to the analysis of the photochemical properties. In this context we designed a novel strategy to access meta-oligoazobiphenyls via site-selective Mills reac...

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Bibliographic Details
Main Authors: Raphael Reuter, Hermann A. Wegner
Format: Article
Language:English
Published: Beilstein-Institut 2012-06-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
azobenzene
cross-coupling reaction
foldamer
molecular switches
photochromism
Online Access:https://doi.org/10.3762/bjoc.8.99
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spelling doaj-f50488c3b3414e63a860a875bfd55e9c2021-02-02T04:39:00ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-06-018187788310.3762/bjoc.8.991860-5397-8-99meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical propertiesRaphael Reuter0Hermann A. Wegner1University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, SwitzerlandUniversity of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056 Basel, SwitzerlandThe investigation of multi-photochromic compounds constitutes a great challenge, not only from a synthetic point of view, but also with respect to the analysis of the photochemical properties. In this context we designed a novel strategy to access meta-oligoazobiphenyls via site-selective Mills reaction and Suzuki cross-coupling in a highly efficient iterative way. Photochemical examination of the resulting monomeric and oligomeric azo compounds revealed that the overall degree of switching was independent of the connected azo-units. However, one of the azobonds in the bis-azobiphenyl is isomerized preferentially despite the high structural similarity.https://doi.org/10.3762/bjoc.8.99azobenzenecross-coupling reactionfoldamermolecular switchesphotochromism
collection DOAJ
language English
format Article
sources DOAJ
author Raphael Reuter
Hermann A. Wegner
spellingShingle Raphael Reuter
Hermann A. Wegner
meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical properties
Beilstein Journal of Organic Chemistry
azobenzene
cross-coupling reaction
foldamer
molecular switches
photochromism
author_facet Raphael Reuter
Hermann A. Wegner
author_sort Raphael Reuter
title meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical properties
title_short meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical properties
title_full meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical properties
title_fullStr meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical properties
title_full_unstemmed meta-Oligoazobiphenyls – synthesis via site-selective Mills reaction and photochemical properties
title_sort meta-oligoazobiphenyls – synthesis via site-selective mills reaction and photochemical properties
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2012-06-01
description The investigation of multi-photochromic compounds constitutes a great challenge, not only from a synthetic point of view, but also with respect to the analysis of the photochemical properties. In this context we designed a novel strategy to access meta-oligoazobiphenyls via site-selective Mills reaction and Suzuki cross-coupling in a highly efficient iterative way. Photochemical examination of the resulting monomeric and oligomeric azo compounds revealed that the overall degree of switching was independent of the connected azo-units. However, one of the azobonds in the bis-azobiphenyl is isomerized preferentially despite the high structural similarity.
topic azobenzene
cross-coupling reaction
foldamer
molecular switches
photochromism
url https://doi.org/10.3762/bjoc.8.99
work_keys_str_mv AT raphaelreuter metaoligoazobiphenylssynthesisviasiteselectivemillsreactionandphotochemicalproperties
AT hermannawegner metaoligoazobiphenylssynthesisviasiteselectivemillsreactionandphotochemicalproperties
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