To Isomerize or not to Isomerize? E/Z Isomers of Cyclic Azobenzene Derivatives and Their Reactivity Upon One‐Electron Reduction

Azo compounds are efficient electron acceptors. Upon one‐electron reduction they generally isomerize forming the thermodynamically most stable radical anion. Herein we show that the size of the central ring in 1,2‐diazocines and diazonines has a ruling influence on the configuration of the one‐elect...

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Bibliographic Details
Published in:Chemistry : a European journal 2023-06, Vol.29 (35), p.e202300146-n/a
Main Authors: Glotz, Gabriel, Knaipp, Konstantin, Maier, Martin S., Hüll, Katharina, Novak, Alexander, Kelterer, Anne‐Marie, Griebenow, Thomas, Herges, Rainer, Trauner, Dirk, Gescheidt, Georg
Format: Article
Language:English
Subjects:
Azo compounds
Chemistry
Configurations
cyclic azobenzenes
EPR isomerization
Isomerization
Isomers
one electron reduction
radical anions
Reduction
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Summary:Azo compounds are efficient electron acceptors. Upon one‐electron reduction they generally isomerize forming the thermodynamically most stable radical anion. Herein we show that the size of the central ring in 1,2‐diazocines and diazonines has a ruling influence on the configuration of the one‐electron reduced species. Markedly, diazonines, which bear a central nine membered heterocycle, show light‐induced E/Z isomerization, but retain the configuration of the diazene N=N moiety upon one‐electron reduction. Accordingly, E/Z isomerization is not induced by reduction. One‐electron reduction of azo compounds generally results in isomerization forming the thermodynamically most stable radical anion. It is shown that the size of the central ring in 1,2‐diazocines and diazonines has a ruling influence on the configuration of the one‐electron reduced species.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202300146