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

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.

Automated summary

This study reports the synthesis, characterization, and application of a library of 26 donor-acceptor (D-A) compounds based on the benzo[c][1,2,5]thiadiazole (BTZ) motif. By varying the donor groups while keeping the BTZ acceptor group the same, the optoelectronic and photophysical properties of the photocatalysts were systematically modified. These photocatalysts were validated through a test reaction under both batch and continuous flow conditions.