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Updated: Jan 2, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
An N-Heterocyclic-Carbene-Derived Distonic Radical Cation
Nolan M Gallagher1, Hong-Zhou Ye1, Shuting Feng2,3
1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139, USA.
Abstract:
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.
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