TY - JOUR
T1 - Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N-Heterocyclic Olefins
AU - Eymann, Leónard Y.M.
AU - Varava, Paul
AU - Shved, Andrei M.
AU - Curchod, Basile F.E.
AU - Liu, Yizhu
AU - Planes, Ophélie M.
AU - Sienkiewicz, Andrzej
AU - Scopelliti, Rosario
AU - Fadaei Tirani, Farzaneh
AU - Severin, Kay
N1 - Funding Information:
The work was supported by the Swiss National Science Foundation and EPFL.
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/10/30
Y1 - 2019/10/30
N2 - The reaction of nitrous oxide (N2O) with N-heterocyclic olefins (NHOs) results in cleavage of the N-O bond and formation of azo-bridged NHO dimers. The latter represent very electron-rich compounds with a low ionization energy. Cyclic voltammetry studies show that the dimers can be classified as new organic super-electron-donors, with a reducing power similar to what is found for tetraazafulvalene derivatives. Mild oxidants are able to convert the neutral dimers into radical cations, which can be isolated. Further oxidation gives stable dications.
AB - The reaction of nitrous oxide (N2O) with N-heterocyclic olefins (NHOs) results in cleavage of the N-O bond and formation of azo-bridged NHO dimers. The latter represent very electron-rich compounds with a low ionization energy. Cyclic voltammetry studies show that the dimers can be classified as new organic super-electron-donors, with a reducing power similar to what is found for tetraazafulvalene derivatives. Mild oxidants are able to convert the neutral dimers into radical cations, which can be isolated. Further oxidation gives stable dications.
UR - http://www.scopus.com/inward/record.url?scp=85073830265&partnerID=8YFLogxK
U2 - 10.1021/jacs.9b10660
DO - 10.1021/jacs.9b10660
M3 - Article (Academic Journal)
C2 - 31621312
AN - SCOPUS:85073830265
SN - 0002-7863
VL - 141
SP - 17112
EP - 17116
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 43
ER -