Structural characterization of quaterphenyl cation radical:: X-ray crystallographic evidence of quinoidal charge delocalization in poly-p-phenylene cation radicals

Quaterphenyl derivative (QP) containing tert-butyl solubilizing groups at the terminal positions yields a stable cation radical salt that was isolated, and its structure was established by X-ray crystallography. The crystal structure of neutral QP and its cation radical (QP(+center dot) SbCl6-) provides unequivocal evidence for the quinoidal stabilization of the cationic charge or polaron by smoothing out the torsional motion of the interconnected p-phenylene rings. Such an observation of stabilization of the cationic charge in a poly-p-phenylene (PPP) derivative forms the basis for the noted high conductivities in PPP oligomers in their doped state.