Photoinduced Electron Transfer-Promoted Reactions Using Exciplex-Type Organic Photoredox Catalyst Directly Linking Donor and Acceptor Arenes

Mugen Yamawaki; Akiko Asano; Toshiki Furutani; Yuki Izumi; Yosuke Tanaka; Kazuyuki Osaka; Toshio Morita; Yasuharu Yoshimi

doi:10.3390/molecules24244453

Photoinduced Electron Transfer-Promoted Reactions Using Exciplex-Type Organic Photoredox Catalyst Directly Linking Donor and Acceptor Arenes

Molecules. 2019 Dec 5;24(24):4453. doi: 10.3390/molecules24244453.

Authors

Mugen Yamawaki¹, Akiko Asano¹, Toshiki Furutani¹, Yuki Izumi¹, Yosuke Tanaka¹, Kazuyuki Osaka¹, Toshio Morita¹, Yasuharu Yoshimi¹

Affiliation

¹ Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui 910-8507, Japan.

Abstract

Directly linked donor and acceptor arenes, such as phenanthrene/naphthalene/biphenyl and 1,3-dicyanobenzene were found to work as photoredox catalysts in the photoreactions of indene, 2,3-dimethyl-2-butene, and 4-methoxyphenylacetic acid. The new stable organic photocatalyst forms an intramolecular exciplex (excited complex) when irradiated in a polar solvent and shows redox catalyst activity, even at low concentrations. To the best of our knowledge, this is the first example of an intramolecular exciplex working as a redox catalyst.

Keywords: cross-coupling between alkenes; directly linking between donor and acceptor arenes; exciplex-type redox catalyst; organic photoredox catalyst; photoinduced decarboxylation; photoinduced electron transfer reaction.

MeSH terms

Catalysis
Naphthalenes / chemistry*
Nitriles / chemistry*
Oxidation-Reduction
Phenanthrenes / chemistry*
Photochemical Processes*

Substances

Naphthalenes
Nitriles
Phenanthrenes
naphthalene
phenanthrene
1,3-dicyanobenzene