Supramolecular Photocatalysis by Utilizing the Host-Guest Charge-Transfer Interaction: Visible-Light-Induced Generation of Triplet Anthracenes for [4+2] Cycloaddition Reactions

Tatsuhiro Uchikura; Mari Oshima; Minami Kawasaki; Kohei Takahashi; Nobuharu Iwasawa

doi:10.1002/anie.201916732

Supramolecular Photocatalysis by Utilizing the Host-Guest Charge-Transfer Interaction: Visible-Light-Induced Generation of Triplet Anthracenes for [4+2] Cycloaddition Reactions

Angew Chem Int Ed Engl. 2020 May 4;59(19):7403-7408. doi: 10.1002/anie.201916732. Epub 2020 Mar 17.

Authors

Tatsuhiro Uchikura^{1

2}, Mari Oshima¹, Minami Kawasaki¹, Kohei Takahashi¹, Nobuharu Iwasawa¹

Affiliations

¹ Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
² Present address: Department of Chemistry, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo, 171-8588, Japan.

PMID: 32043287
DOI: 10.1002/anie.201916732

Abstract

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.

Keywords: anthracene; charge-transfer interactions; photocatalysis; supramolecular catalysts; triplet excited state.

Grants and funding

15H05800/Japan Society for the Promotion of Science