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

Fingerprint

Click Chemistry
tethering
hydrazides
Isomerization
Emulsions
aldehydes
Aldehydes
Surface-Active Agents
isomerization
emulsions
Oxidation-Reduction
alcohols
surfactants
chemistry
azobenzene
4-nitrobenzyl alcohol

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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 journalArticle

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.
@article{ea88bd9f293e49d7a2f1ce7b438a326a,
title = "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.",
author = "Zhu, {Jie S.} and Larach, {Julio M.} and Tombari, {Robert J.} and Gingrich, {Phillip W.} and Bode, {Stanley R.} and Tuck, {Jeremy R.} and Warren, {Hunter T.} and Son, {Jung Ho} and Duim, {Whitney C.} and Fettinger, {James C.} and Haddadin, {Makhluf J.} and Tantillo, {Dean J.} and Kurth, {Mark J.} and Olson, {David E.}",
year = "2019",
month = "11",
day = "1",
doi = "10.1021/acs.orglett.9b03387",
language = "English (US)",
volume = "21",
pages = "8765--8770",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "21",

}

TY - JOUR

T1 - A Redox Isomerization Strategy for Accessing Modular Azobenzene Photoswitches with near Quantitative Bidirectional Photoconversion

AU - Zhu, Jie S.

AU - Larach, Julio M.

AU - Tombari, Robert J.

AU - Gingrich, Phillip W.

AU - Bode, Stanley R.

AU - Tuck, Jeremy R.

AU - Warren, Hunter T.

AU - Son, Jung Ho

AU - Duim, Whitney C.

AU - Fettinger, James C.

AU - Haddadin, Makhluf J.

AU - Tantillo, Dean J.

AU - Kurth, Mark J.

AU - Olson, David E.

PY - 2019/11/1

Y1 - 2019/11/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85074294690&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85074294690&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b03387

DO - 10.1021/acs.orglett.9b03387

M3 - Article

C2 - 31638403

AN - SCOPUS:85074294690

VL - 21

SP - 8765

EP - 8770

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 21

ER -