Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer.

Mikkel Krell-Jørgensen Habiburrahman ZulfikriMagnus Grage BonnevieFrederik Simonsen Bro Asmus Ougaard Dohn Luca Laraia

Published in: Chemical communications (Cambridge, England) (2023)

We report bistable indole-containing hemithioindigos (HTIs) with one-way quantitative photoswitching properties. Supported by state-averaged CASPT2/CASSCF calculations, we propose a mechanism for the observed one-way photoswitching that involves an isomer-specific excited state intramolecular proton transfer (ESIPT). Additionally, we developed a thermally bistable oligomer-inspired bipyrrole-containing HTI, which displays large band separation and bidirectional near-quantitative photoisomerization in the near-infrared, bio-optical window.

Keyphrases

high resolution
electron transfer
molecular dynamics
fluorescent probe
high speed
quantum dots