Fluorinated analogs of polyhedral hydrocarbons, namely polyhedral fluorocarbon, have been predicted to localize an electron within their cages upon reduction, which arises from a stabilized vacant orbital within the cage derived from multiple σ* orbitals of C–F bonds. This internal localization of electrons stands in stark contrast to common π-conjugated electron acceptors, which usually host electrons on their molecular surfaces. In the present study, we achieved the synthesis and characterization of perfluorocubane, a stable polyhedral fluorocarbon (Science, 2022, 377, 756–759.). The key to the successful synthesis was the efficient introduction of multiple fluorine atoms to cubane by liquid-phase reaction with fluorine gas. The solid-state structure of perfluorocubane was confirmed using x-ray crystallography, and its electron-accepting character was corroborated electrochemically and spectroscopically. The radical anion of perfluorocubane was examined by matrix-isolation electron spin resonance spectroscopy, which revealed that the unpaired electron accepted by perfluorocubane is located predominantly inside the cage.

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