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Supramolecular Photocatalysis by Utilizing the Host–Guest Charge‐Transfer Interaction: Visible‐Light‐Induced Generation of Triplet Anthracenes for [4+2] Cycloaddition Reactions
Author(s) -
Uchikura Tatsuhiro,
Oshima Mari,
Kawasaki Minami,
Takahashi Kohei,
Iwasawa Nobuharu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201916732
Subject(s) - anthracene , photochemistry , cycloaddition , excited state , chemistry , photocatalysis , supramolecular chemistry , electron transfer , visible spectrum , triplet state , catalysis , crystal structure , materials science , organic chemistry , molecule , optoelectronics , physics , nuclear physics
Supramolecular photocatalysis via charge‐transfer excitation of a host–guest complex was developed by use of the macrocyclic boronic ester [2+2] BTH‐F containing highly electron‐deficient difluorobenzothiadiazole moieties. In the presence of a catalytic amount of [2+2] BTH‐F , the triplet excited state of anthracene was generated from the charge‐transfer excited state of anthracene@[2+2] BTH‐F by visible‐light irradiation, and cycloaddition of the excited anthracene with several dienes and alkenes proceeded in a [4+2] manner in high yields.