Radical Cation and Dication of Fluorene Fully Annelated with Bicyclo[2.2.2]octene Units: Importance of the Quinoidal Resonance Structure in the Cationic Fluorene

Fluorene 1 fully annelated with bicyclo[2.2.2]octene units was newly synthesized and oxidized to stable cationic species. The structure of
radical cation salt 1•+SbCl6- was determined by X-ray crystallography, while the first fluorene dication 12+ was characterized by 1H and 13C
NMR at −80 °C. Combined with the results of theoretical calculations, an important contribution of a quinoidal structure to the resonance
hybrid was demonstrated in both 1•+ and 12+.