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

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 < 0.25 V). Here we show that a hybrid BN/carbene approach allows access to an unsymmetrical analogue of Thiele's hydrocarbon 1, and that this strategy confers markedly enhanced stability on the radical cation. 1^•+ is stable across an exceptionally wide redox range (> 1 V), permitting its isolation in crystalline form. Further single-electron oxidation affords borenium

SUBMITTER: Loh YK 

PROVIDER: S-EPMC8642399 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature