Cyclization from Higher Excited States of Diarylethenes Having a Substituted Azulene Ring.
azulene
cyclization
density functional calculations
electronic structures
photochromism
substituent effects
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
04 Sep 2020
04 Sep 2020
Historique:
received:
07
04
2020
revised:
18
05
2020
pubmed:
21
5
2020
medline:
21
5
2020
entrez:
21
5
2020
Statut:
ppublish
Résumé
The cyclization reaction of diarylethenes having an azulene ring occurs only via higher excited states. Novel diarylethenes having an azulene ring with a strong donor or acceptor were synthesized and examined in these reactions. A derivative having an electron-donating 1,3-benzodithiol-2-ylidenemethyl group at the 1-position of the azulene ring showed photochromism, whereas neither a derivative having a π-conjugated electron-donating group at the 3-position of the azulene ring nor derivatives having a π-conjugated electron-withdrawing group at the 1- or 3-position of the azulene ring showed any photochromism. The photoreactivities of these compounds were explained by calculating forces and bond orders on the excited states using density functional theory (DFT) and time-dependent (TD)-DFT.
Identifiants
pubmed: 32432373
doi: 10.1002/chem.202001671
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11441-11450Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP26107012
Organisme : Japan Science and Technology Agency
ID : JPMJCR17N2
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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