Issue 39, 2022

Fast relaxing red and near-IR switchable azobenzenes with chalcogen and halogen substituents: periodic trends, tuneable thermal half-lives and chalcogen bonding

Abstract

Molecular photoswitches operating in the red to near-IR region with controllable thermal relaxation rates are attractive components for photo-regulating biological processes. Herein, we report the synthesis of red-shifted azobenzenes functionalised with the heavier chalcogens and halogens that meet these requirements for biological application; namely fatigue-resistant photo-switching with red and near IR light and functional handles for further functionalisation for application. We report robust periodic trends for the chalcogen and halogen azobenzene series, and exploit intramolecular chalcogen bonding to tune and redshift the absorption maxima, supported by photo-physical measurements and solid-state structural analysis. Remarkably, the rate of the ZE thermal isomerisation can be tuned over timescales spanning 107 s by judicious choice of chalcogen and halogen substituents.

Graphical abstract: Fast relaxing red and near-IR switchable azobenzenes with chalcogen and halogen substituents: periodic trends, tuneable thermal half-lives and chalcogen bonding

Supplementary files

Article information

Article type
Edge Article
Submitted
17 aug 2022
Accepted
18 sep 2022
First published
20 sep 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 11551-11559

Fast relaxing red and near-IR switchable azobenzenes with chalcogen and halogen substituents: periodic trends, tuneable thermal half-lives and chalcogen bonding

A. Kerckhoffs, K. E. Christensen and M. J. Langton, Chem. Sci., 2022, 13, 11551 DOI: 10.1039/D2SC04601F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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