A Modular Approach to Arylazo-1,2,3-triazole Photoswitches

Jeremy R. Tuck, Robert J. Tombari, Noah Yardeny, David E. Olson

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
JournalOrganic Letters
DOIs
StateAccepted/In press - 2021

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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