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An N-Heterocyclic-Carbene-Derived Distonic Radical Cation |
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| Authors: | Nolan M Gallagher Hong-Zhou Ye Shuting Feng Jeffrey Lopez Yun Guang Zhu Troy Van Voorhis Yang Shao-Horn Jeremiah A Johnson |
| Institution: | 1. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139 USA;2. Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139 USA;3. Research Laboratory of Electronics, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139 USA;4. Research Laboratory of Electronics, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139 USA
Departments of Mechanical Engineering and Materials Science and Engineering, 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. |
| Keywords: | Carbodiimide Kationen N-Heterocyclische Carbene Radikale Zwitterionische Addukte |