Multiple stable redox states and tunable ground states via the marriage of viologens and Chichibabin's hydrocarbon.

ABSTRACT: Chichibabin's hydrocarbon and viologens are among the most famous diradicaloids and organic redox systems, respectively. However, each has its own disadvantages: the instability of the former and its charged species, and the closed-shell nature of the neutral species derived from the latter, respectively. Herein, we report that terminal borylation and central distortion of 4,4'-bipyridine allow us to readily isolate the first bis-BN-based analogues (1 and 2) of Chichibabin's hydrocarbon with three stable redox states and tunable ground states. Electrochemically, both compounds exhibit two reversible oxidation processes with wide redox ranges. One- and two-electron chemical oxidations of 1 afford the crystalline radical cation 1˙⁺ and dication 1²⁺, respectively. Moreov

SUBMITTER: Dai Y 

PROVIDER: S-EPMC10056129 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature