Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N-Heterocyclic Olefins

Leónard Y.M. Eymann; Paul Varava; Andrei M. Shved; Basile F.E. Curchod; Yizhu Liu; Ophélie M. Planes; Andrzej Sienkiewicz; Rosario Scopelliti; Farzaneh Fadaei Tirani; Kay Severin

doi:10.1021/jacs.9b10660

Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N-Heterocyclic Olefins

Leónard Y.M. Eymann, Paul Varava, Andrei M. Shved, Basile F.E. Curchod, Yizhu Liu, Ophélie M. Planes, Andrzej Sienkiewicz, Rosario Scopelliti, Farzaneh Fadaei Tirani, Kay Severin^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

50 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	17112-17116
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	141
Issue number	43
DOIs	https://doi.org/10.1021/jacs.9b10660
Publication status	Published - 30 Oct 2019

Bibliographical note

Funding Information:
The work was supported by the Swiss National Science Foundation and EPFL.

Publisher Copyright:
© 2019 American Chemical Society.

Research Groups and Themes

Physical & Theoretical

Access to Document

10.1021/jacs.9b10660

Handle.net

Persistent link

Cite this

@article{491309d64fb144c39fa9600dda86951c,

title = "Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N-Heterocyclic Olefins",

abstract = "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.",

author = "Eymann, \{Le{\'o}nard Y.M.\} and Paul Varava and Shved, \{Andrei M.\} and Curchod, \{Basile F.E.\} and Yizhu Liu and Planes, \{Oph{\'e}lie M.\} and Andrzej Sienkiewicz and Rosario Scopelliti and \{Fadaei Tirani\}, Farzaneh and Kay Severin",

note = "Funding Information: The work was supported by the Swiss National Science Foundation and EPFL. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = oct,

day = "30",

doi = "10.1021/jacs.9b10660",

language = "English",

volume = "141",

pages = "17112--17116",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "43",

}

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

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 - https://www.scopus.com/pages/publications/85073830265

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 -

Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N-Heterocyclic Olefins

Abstract

Bibliographical note

Research Groups and Themes

Access to Document

Handle.net

Other files and links

Fingerprint

Cite this