Redshifted and thermally bistable one-way quantitative hemithioindigo-derived photoswitches enabled by isomer-specific excited state intramolecular proton transfer
Mikkel Krell-Jørgensen, Habiburrahman Zulfikri, Magnus Grage Bonnevie, Frederik Simonsen Bro, Asmus Ougaard Dohn, Luca Laraia
Abstract
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.
Topics & Concepts
PhotoisomerizationBistabilityIntramolecular forceExcited stateOligomerPhotochemistryChemistryChemical physicsProtonIsomerizationMaterials scienceOptoelectronicsAtomic physicsPolymer chemistryPhysicsStereochemistryBiochemistryQuantum mechanicsCatalysisPhotochromic and Fluorescence ChemistryPhotoreceptor and optogenetics researchRadical Photochemical Reactions