An N-Heterocyclic-Carbene-Derived Distonic Radical Cation

Nolan M. Gallagher, Hong Zhou Ye, Shuting Feng, Jeffrey Lopez, Yun Guang Zhu, Troy Van Voorhis, Yang Shao-Horn, Jeremiah A. Johnson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)3952-3955
Number of pages4
JournalAngewandte Chemie - International Edition
Volume59
Issue number10
DOIs
StatePublished - Mar 2 2020

Keywords

  • N-heterocyclic carbenes
  • carbodiimides
  • cations
  • radicals
  • zwitterionic adducts

ASJC Scopus subject areas

  • General Chemistry
  • Catalysis

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