Structural Characterization of Quaterphenyl Cation Radical:  X-ray Crystallographic Evidence of Quinoidal Charge Delocalization in Poly-p-phenylene Cation Radicals

Document Type

Article

Language

eng

Publication Date

2007

Publisher

American Chemical Society

Source Publication

Journal of the American Chemical Society

Source ISSN

0002-7863

Original Item ID

doi:10.1021/ja0720356

Abstract

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+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.

Comments

Accepted version. Journal of the American Chemical Society, Vol. 129, No. 26 (2007): 8070-8071. DOI. © 2007 American Chemical Society. Used with permission.

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