Photoswitches capable of accessing two geometric states are highly desirable, especially if their design is modular and incorporates a pharmacophore tethering site. We utilized azide-alkyne click chemistry to access arylazo-1,2,3-triazoles, a previously unexplored class of azoheteroarenes that exhibit high thermal stabilities and near quantitative bidirectional photoconversion. Our strategy enabled us to access a wide variety of photoswitchable compounds from readily available azides. In a similar fashion, we developed a redox isomerization strategy for synthesizing <i>p</i>-formylazobenzenes from <i>p</i>-nitrobenzyl alcohol, where the resulting azo-aldehydes can be readily converted to photoswitchable compounds with excellent photophysical properties using simple hydrazide click chemistry. The ability to streamline syntheses of photoswitchable compounds with reliably optimal photophysical properties allows us to investigate the mechanism of action of various small molecules in biological systems with the high degree of spatial and temporal control that the field of photopharmacology offers.

Novel scaffolds for photoswitchable tools

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.