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

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.

SUBMITTER: Zhu JS

PROVIDER: S-EPMC7158698 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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

Zhu Jie S JS Larach Julio M JM Tombari Robert J RJ Gingrich Phillip W PW Bode Stanley R SR Tuck Jeremy R JR Warren Hunter T HT Son Jung-Ho JH Duim Whitney C WC Fettinger James C JC Haddadin Makhluf J MJ Tantillo Dean J DJ Kurth Mark J MJ Olson David E DE

Organic letters 20191022 21

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 <i>p</i>-formylazobenzenes from <i>p</i>-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 photoswit ...[more]

PMID: 31638403

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