American Chemical Society
ol026841n_si_002.cif (60.1 kB)

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

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posted on 2002-10-19, 00:00 authored by Tohru Nishinaga, Ryota Inoue, Akira Matsuura, Koichi Komatsu
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+.