α,α′-Diamino‑<i>p</i>‑tetrafluoroquinodimethane: Stability of One- and Two-Electron Oxidized Species and Fixation of Molecular Oxygen

Herein, we report the synthesis, characterization, and reactivity of α,α′-diamino-p-tetrafluoroquinodimethane, a p-tetrafluorophenylene-bridged monosubstituted carbene-based Thiele’s hydrocarbon A. The compound exhibits a reversible two-step one-electron oxidation with a marginally stable radical cation state B. The in situ formation of the radical cation could be confirmed by electron paramagnetic resonance spectroscopy. Interestingly, α,α′-diamino-p-tetrafluoroquinodimethane fixates atmospheric oxygen to form a 16-membered peroxide-bridged macrocyclic compound C.