Stenhouse Salts: Visible Light Photoswitches for Protic Environments

Abstract

Designing photoswitches that have large structural changes, are visible-light responsive, and are compatible with water is a major challenge for moving toward applications in biological systems. Despite the potential for Stenhouse salts to be a water-compatible counterpart to the popular DASA photoswitches, there has not yet been any major investigation into their properties as a photoswitch. Here, we report a series of aniline-based Stenhouse salt (AnSten) photoswitches with electron donating and withdrawing groups. AnSten photoswitches reversibly switch from a visible light absorbing isomer to a visible light transparent isomer upon irradiation with green light. The dark equilibrium and switching kinetics are dependent on the electronics of the aniline. These molecules switch reversibly in common protic solvents including water and hydrogels. Stenhouse salts show significant potential as a visible light active, water compatible, negative photochromic, T-type photoswitch with a large structural change.