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

Dominic Taylor; Thomas Malcomson; Adilet Zhakeyev; Shengxian Cheng; Georgina M. Rosair; Jose Marques-Hueso; Zhengtao Xu; Martin J. Paterson; Scott J. Dalgarno; Filipe Vilela

doi:10.1039/D2QO01316A

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

Dominic Taylor,

^a Thomas Malcomson,

^b Adilet Zhakeyev,^c Shengxian Cheng,^d Georgina M. Rosair,

^a Jose Marques-Hueso,

^c Zhengtao Xu,^e Martin J. Paterson,

^a Scott J. Dalgarno

*^a and Filipe Vilela

*^a

Author affiliations

* Corresponding authors

^a Institute of Chemical Sciences, School of Engineering and Physical Science, Heriot-Watt University, Riccarton, Edinburgh, UK
E-mail: S.J.Dalgarno@hw.ac.uk, F.Vilela@hw.ac.uk

^b Department of Chemistry, Lancaster University, Lancaster, UK

^c Institute of Sensors, Signals and Systems, School of Engineering and Physical Science, Heriot-Watt University, Riccarton, Edinburgh, UK

^d Department of Chemistry, City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, Hong Kong

^e Institute of Materials Research and Engineering (IMRE), Agency of Science, Technology and Research (A*STAR), 2 Fusionopolis Way, Innovis, Singapore 138634

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.

This article is part of the themed collection: In memory of John S. Fossey – CAtalysis and SEnsing (CASE)

Organic Chemistry Frontiers

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

Abstract

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

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