"Click-switch" - one-step conversion of organic azides into photochromic diarylethenes for the generation of light-controlled systems.

ABSTRACT: Diarylethenes (DAEs) are an established class of photochromic molecules, but their effective incorporation into pre-existing targets is synthetically difficult. Here we describe a new class of DAEs in which one of the aryl rings is a 1,2,3-triazole that is formed by "click" chemistry between an azide on the target and a matching alkyne-cyclopentene-thiophene component. This late-stage zero-length linking allows for tight integration of the DAE with the target, thereby increasing the chances for photomodulation of target functions. Nineteen different DAEs were synthesized and their properties investigated. All showed photochromism. Electron-withdrawing groups, and in particular -M-substituents at the triazole and/or thiophene moiety resulted in DAEs with high photo- and thermostability. Fur

SUBMITTER: Becht S 

PROVIDER: S-EPMC8447918 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature