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

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journal contribution
posted on 2019-10-22, 12:40 authored by 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
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.