Issue 42, 2022

A bis-NHC–CAAC dimer derived dicationic diradical

Abstract

The isolation of carbon-centered diradicals is always challenging due to synthetic difficulties and their limited stability. Herein we report the synthesis of a trans-1,4-cyclohexylene bridged bis-NHC–CAAC dimer derived thermally stable dicationic diradical. The diradical character of this compound was confirmed by EPR spectroscopy. The variable temperature EPR study suggests the singlet state to be marginally more stable than the triplet state (2J = −5.5 cm−1EST = 0.065 kJ mol−1)). The presence of the trans-1,4-cyclohexylene bridge is instrumental for the successful isolation of this dicationic diradical. Notably, in the case of ethylene or propylene bridged bis-NHC–CAAC dimers, the corresponding dicationic diradicals are transient and rearrange to hydrogen abstracted products.

Graphical abstract: A bis-NHC–CAAC dimer derived dicationic diradical

Supplementary files

Article information

Article type
Edge Article
Submitted
14 Jul 2022
Accepted
21 Sep 2022
First published
21 Sep 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 12533-12539

A bis-NHC–CAAC dimer derived dicationic diradical

M. K. Nayak, P. Sarkar, B. J. Elvers, S. Mehta, F. Zhang, N. Chrysochos, I. Krummenacher, T. Vijayakanth, R. S. Narayanan, R. Dolai, B. Roy, V. Malik, H. Rawat, A. Mondal, R. Boomishankar, S. K. Pati, H. Braunschweig, C. Schulzke, P. Ravat and A. Jana, Chem. Sci., 2022, 13, 12533 DOI: 10.1039/D2SC03937K

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