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