Open AccessA Modular Approach to Arylazo-1,2,3-triazole Photoswitches
Author(s) -
Jeremy R. Tuck,
Robert J. Tombari,
Noah Yardeny,
David E. Olson
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c01230
Subject(s) - chemistry , click chemistry , modular design , combinatorial chemistry , azide , triazole , alkyne , class (philosophy) , nanotechnology , catalysis , computer science , organic chemistry , programming language , materials science , artificial intelligence
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.