4.7 Article

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

Journal

CHEMICAL COMMUNICATIONS
Volume 59, Issue 5, Pages 563-566

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc05548a

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We report bistable indole-containing hemithioindigos (HTIs) with one-way quantitative photoswitching properties. A mechanism involving isomer-specific excited state intramolecular proton transfer (ESIPT) is proposed based on calculations. We also developed a thermally bistable oligomer-inspired bipyrrole-containing HTI that exhibits large band separation and bidirectional near-quantitative photoisomerization in the near-infrared, bio-optical window.
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.

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