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Cyclization from Higher Excited States of Diarylethenes Having a Substituted Azulene Ring
Author(s) -
Hattori Yohei,
Maejima Tatsuya,
Sawae Yumi,
Kitai Junichiro,
Morimoto Masakazu,
Toyoda Ryojun,
Nishihara Hiroshi,
Yokojima Satoshi,
Nakamura Shinichiro,
Uchida Kingo
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001671
Subject(s) - azulene , excited state , ring (chemistry) , chemistry , photochemistry , physics , atomic physics , organic chemistry
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.