A crystalline radical cation derived from Thiele’s hydrocarbon with redox range beyond 1 V

Ying Kai Loh, Petra Vasko, Caitilín McManus, Andreas Heilmann, William K. Myers and Simon Aldridge ()
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Ying Kai Loh: University of Oxford
Petra Vasko: University of Jyväskylä
Caitilín McManus: University of Oxford
Andreas Heilmann: University of Oxford
William K. Myers: University of Oxford
Simon Aldridge: University of Oxford

Nature Communications, 2021, vol. 12, issue 1, 1-7

Abstract: Abstract Thiele’s hydrocarbon occupies a central role as an open-shell platform for new organic materials, however little is known about its redox behaviour. While recent synthetic approaches involving symmetrical carbene substitution of the CPh2 termini yield isolable neutral/dicationic analogues, the intervening radical cations are much more difficult to isolate, due to narrow compatible redox ranges (typically 1 V), permitting its isolation in crystalline form. Further single-electron oxidation affords borenium dication 12+, thereby establishing an organoboron redox system fully characterized in all three redox states. We perceive that this strategy can be extended to other transient organic radicals to widen their redox stability window and facilitate their isolation.

Date: 2021
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DOI: 10.1038/s41467-021-27104-y

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