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

doi:10.1021/acs.orglett.9b03387

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

Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Pages (from-to)	8765-8770
Number of pages	6
Journal	Organic Letters
Volume	21
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.9b03387
State	Published - 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

A Redox Isomerization Strategy for Accessing Modular Azobenzene Photoswitches with near Quantitative Bidirectional Photoconversion. / Zhu, Jie S.; Larach, Julio M.; Tombari, Robert J.; Gingrich, Phillip W.; Bode, Stanley R.; Tuck, Jeremy R.; Warren, Hunter T.; Son, Jung Ho; Duim, Whitney C.; Fettinger, James C.; Haddadin, Makhluf J.; Tantillo, Dean J.; Kurth, Mark J.; Olson, David E.

In: Organic Letters, Vol. 21, No. 21, 01.11.2019, p. 8765-8770.

Research output: Contribution to journal › Article

Zhu, JS, Larach, JM, Tombari, RJ, Gingrich, PW, Bode, SR, Tuck, JR, Warren, HT, Son, JH, Duim, WC, Fettinger, JC, Haddadin, MJ, Tantillo, DJ, Kurth, MJ & Olson, DE 2019, 'A Redox Isomerization Strategy for Accessing Modular Azobenzene Photoswitches with near Quantitative Bidirectional Photoconversion', Organic Letters, vol. 21, no. 21, pp. 8765-8770. https://doi.org/10.1021/acs.orglett.9b03387

Zhu, Jie S. ; Larach, Julio M. ; Tombari, Robert J. ; Gingrich, Phillip W. ; Bode, Stanley R. ; Tuck, Jeremy R. ; Warren, Hunter T. ; Son, Jung Ho ; Duim, Whitney C. ; Fettinger, James C. ; Haddadin, Makhluf J. ; Tantillo, Dean J. ; Kurth, Mark J. ; Olson, David E. / A Redox Isomerization Strategy for Accessing Modular Azobenzene Photoswitches with near Quantitative Bidirectional Photoconversion. In: Organic Letters. 2019 ; Vol. 21, No. 21. pp. 8765-8770.

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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.",

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