Aurones: Unexplored Visible‐Light Photoswitches for Aqueous Medium

Abstract

The development of synthetically accessible photoswitches showing an efficient performance in aqueous medium has recently become an urgent task due to the rapid progress of photopharmacology and novel biomedical applications. In response to this challenge, in this work, aurone derivatives are introduced as a novel class of efficient visible‐light photoswitches for aqueous medium. In general, aurones exhibit superior performance in water, including significantly higher quantum yields, compared with other indigoid photoswitches (hemithioindigo and hemiindigo). Especially remarkable are the half‐lives of the photoinduced E‐isomers of aurones in water, reaching up to 7 years. Further modification of the aurone scaffold with substituents that increase water solubility does not affect most of the photoswitching characteristics and even improves some them. The highly advantageous property profile of the aurone photoswitches make them a perfect novel platform for the design of light‐controllable systems in the areas requiring photoswitching in aqueous medium.

Photochromic derivatives of indigo: historical overview of development, challenges and applications

“…In 1968, Ross and Blanc for the first time applied the Fischer method to calculate the extinction coefficients and quantum yields of the forward and backward isomerization of N,N'-diacetylindigo (9a) in toluene without isolation of the Z-form [49]. The Fischer method remains relevant up to date and is frequently used for the characterization of the photoinduced forms of various indigoid photoswitches [50][51][52][53][54].…”