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 | |
| State | Published - Nov 1 2019 |
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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 journal › Article
}
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 -