Heterocyclic Hemithioindigos: Highly Advantageous Properties as Molecular Photoswitches

25 July 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A survey of heterocyclic hemithioindigo photoswitches is presented identifying a number of structural motives with outstanding property profiles. The highly sought-after combination of pronounced photochromism, quantitative switching in both directions, exceptional high quantum yields, and high thermal stability of metastable states can be realized with 4-imidazole and 3-indole-based derivatives. In the former, an unusual preorganization using isomer selective chalcogen- and hydrogen bonding allows to precisely control geometry changes and tautomerism upon switching. Heterocyclic hemithioindigos thus represent a next-generation of photoswitches with advanced capabilities that will be of great value to anyone interested in establishing defined and reversible control at the molecular level.

Keywords

photoswitch
photochemistry
indigoid
quantum yield
heterocycle
hemithioindigo

Supplementary materials

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Description
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Supporting Information
Description
Details of synthesis, photochemical, photophysical and thermal behavior, and crystal structural data.
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