A Redox Isomerization Strategy for Accessing Modular Azobenzene Photoswitches with near Quantitative Bidirectional Photoconversion

Jie S. Zhu, Julio M. Larach, Robert J. Tombari, Phillip W. Gingrich, Stanley R. Bode, Jeremy R. Tuck, Hunter T. Warren, Jung Ho Son, Whitney C. Duim, James C. Fettinger, Makhluf J. Haddadin, Dean J. Tantillo, Mark J. Kurth, David E. Olson

Research output: Contribution to journalArticle

Abstract

Photoswitches capable of accessing two geometric states are highly desirable, especially if their design is modular and incorporates a pharmacophore tethering site. We describe a redox isomerization strategy for synthesizing p-formylazobenzenes from p-nitrobenzyl alcohol. The resulting azo-aldehydes can be readily converted to photoswitchable compounds with excellent photophysical properties using simple hydrazide click chemistry. As a proof of principle, we synthesized a photoswitchable surfactant enabling the photocontrol of an emulsion with exceptionally high spatiotemporal precision.

Original languageEnglish (US)
Pages (from-to)8765-8770
Number of pages6
JournalOrganic Letters
Volume21
Issue number21
DOIs
StatePublished - Nov 1 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Zhu, J. S., Larach, J. M., Tombari, R. J., Gingrich, P. W., Bode, S. R., Tuck, J. R., Warren, H. T., Son, J. H., Duim, W. C., Fettinger, J. C., Haddadin, M. J., Tantillo, D. J., Kurth, M. J., & Olson, D. E. (2019). A Redox Isomerization Strategy for Accessing Modular Azobenzene Photoswitches with near Quantitative Bidirectional Photoconversion. Organic Letters, 21(21), 8765-8770. https://doi.org/10.1021/acs.orglett.9b03387