Issue 20, 2022

4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts

Abstract

Electron donor–acceptor (D–A) systems based on the benzo[c][1,2,5]thiadiazole (BTZ) motif have been extensively researched for use in photovoltaics or as fluorescent sensors. However, their use as potential visible-light organophotocatalysts has not received any in-depth study. Here we report the synthesis, characterisation, and application of a library of 26 D–A compounds based on the BTZ group. By varying the donor groups whilst keeping the BTZ acceptor group the same, we have been able to systematically modify the photocatalyst's optoelectronic and photophysical properties. These photocatalysts were then validated using a Minisci-type decarboxylative alkylation of electron deficient heteroarenes as a test reaction under both batch and continuous flow conditions.

Graphical abstract: 4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts

Supplementary files

Article information

Article type
Research Article
Submitted
17 Aug. 2022
Accepted
19 Aug. 2022
First published
19 Aug. 2022
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2022,9, 5473-5484

4,7-Diarylbenzo[c][1,2,5]thiadiazoles as fluorophores and visible light organophotocatalysts

D. Taylor, T. Malcomson, A. Zhakeyev, S. Cheng, G. M. Rosair, J. Marques-Hueso, Z. Xu, M. J. Paterson, S. J. Dalgarno and F. Vilela, Org. Chem. Front., 2022, 9, 5473 DOI: 10.1039/D2QO01316A

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