A Modular Approach to Arylazo-1,2,3-triazole Photoswitches
Jeremy R. Tuck, Robert J. Tombari, Noah Yardeny, David E. Olson
Abstract
Azoheteroarenes make up an emerging class of photoswitchable compounds with unique photophysical properties and advantages over traditional azobenzenes. Therefore, methods for synthesizing azoheteroarenes are highly desirable. Here, we utilize 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. Controlling the catalyst or 1,3-dipole grants access to both regioisomeric arylazotriazoles and arylazoisoxazoles, highlighting the versatility of our approach.
Topics & Concepts
ChemistryClick chemistryModular designCombinatorial chemistryAzideTriazoleAlkyneNanotechnologyCatalysisComputer scienceOrganic chemistryMaterials scienceProgramming languagePhotochromic and Fluorescence ChemistryClick Chemistry and ApplicationsPhotoreceptor and optogenetics research