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An N‐Heterocyclic‐Carbene‐Derived Distonic Radical Cation
Author(s) -
Gallagher Nolan M.,
Ye HongZhou,
Feng Shuting,
Lopez Jeffrey,
Zhu Yun Guang,
Van Voorhis Troy,
ShaoHorn Yang,
Johnson Jeremiah A.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915534
Subject(s) - carbene , redox , chemistry , adduct , radical ion , photochemistry , carbodiimide , ion , combinatorial chemistry , polymer chemistry , inorganic chemistry , catalysis , organic chemistry
We present the discovery of a novel radical cation formed through one‐electron oxidation of an N‐heterocyclic carbene–carbodiimide (NHC–CDI) zwitterionic adduct. This compound possesses a distonic electronic structure (spatially separate spin and charge regions) and displays persistence under ambient conditions. We demonstrate its application in a redox‐flow battery exhibiting minimal voltage hysteresis, a flat voltage plateau, high Coulombic efficiency, and no performance decay for at least 100 cycles. The chemical tunability of NHCs and CDIs suggests that this approach could provide a general entry to redox‐active NHC–CDI adducts and their persistent radical ions for various applications.