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
• Filipe Vilela^a

• ^aInstitute of Chemical Sciences, School of Engineering and Physical Science, Heriot-Watt University, Riccarton, Edinburgh EH14 4AS, UK.
• ^bDepartment of Chemistry, Lancaster University, Lancaster, LA1 4YB, UK
• ^cInstitute of Sensors, Signals and Systems, School of Engineering and Physical Science, Heriot-Watt University, Riccarton, Edinburgh EH14 4AS, UK
• ^dDepartment of Chemistry, City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, Hong Kong
• ^eInstitute of Materials Research and Engineering (IMRE), Agency of Science, Technology and Research (A*STAR), 2 Fusionopolis Way, Innovis, Singapore 138634

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.

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