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Phenylene-bridged bis(benzimidazolium) (BBIm2+): a dicationic organic photoredox catalyst

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Abstract

A dicationic photoredox catalyst composed of phenylene-bridged bis(benzimidazolium) (BBIm2+) was designed, synthesised and demonstrated to promote the photochemical decarboxylative hydroxylation and dimerisation of carboxylic acids. The catalytic activity of BBIm2+ was higher than that for a monocation analogue, suggesting that the dicationic nature of BBIm2+ plays a key role in these decarboxylative reactions. The rate constant for the decay of the triplet–triplet absorption of the excited BBIm2+ increased with increasing concentration of the carboxylate anion with a saturated dependence, suggesting that photoinduced electron transfer occurs within the ion pair complex composed of the triplet excited state of BBIm2+ and a carboxylate anion.

Graphical abstract: Phenylene-bridged bis(benzimidazolium) (BBIm2+): a dicationic organic photoredox catalyst

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Article information


Submitted
20 Jul 2020
Accepted
07 Oct 2020
First published
07 Oct 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Phenylene-bridged bis(benzimidazolium) (BBIm2+): a dicationic organic photoredox catalyst

T. Kodama, M. Kubo, W. Shinji, K. Ohkubo and M. Tobisu, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC03958F

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