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

doi:10.1039/d2cc05548a

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

Chem Commun (Camb). 2023 Jan 12;59(5):563-566. doi: 10.1039/d2cc05548a.

Authors

Mikkel Krell-Jørgensen¹, Habiburrahman Zulfikri^{2

3}, Magnus Grage Bonnevie¹, Frederik Simonsen Bro¹, Asmus Ougaard Dohn^{2

4}, Luca Laraia¹

Affiliations

¹ Department of Chemistry, Technical University of Denmark, Kemitorvet 2800, Kongens Lyngby, Denmark. luclar@kemi.dtu.dk.
² Science Institute and Faculty of Physical Sciences, University of Iceland, Reykjavík, Iceland.
³ Department of Chemical Engineering, Faculty of Engineering, Universitas Indonesia, Depok 16424, Indonesia.
⁴ Department of Physics, Technical University of Denmark, Fysikvej 2800, Kongens Lyngby, Denmark.

PMID: 36537010
DOI: 10.1039/d2cc05548a

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.