Hopping of a single electron in hexakis-(4-benzoylphenyl)benzene through the hexaphenylbenzene propeller

ORGN 445

Erica Jean Kopatz, erica.kopatz@mu.edu1, Rajendra Rathore, rajendra.rathore@marquette.edu1, and Farooq A Khan, fkhan@westga.edu2. (1) Department of Chemistry, Marquette University, 535 N 14th St, PO Box 1881, Milwaukee, WI 53201, (2) Department of Chemistry, State University of West Georgia, Carrollton, GA 30118
Propeller-like arrangement of phenyl groups in hexaphenylbenzene allows an effective electronic coupling amongst the six aryl rings via an overlap of orbitals on carbon 1 of phenyls that lie cofacially at a close distance of 2.9 angstroms from each other (A). Herein, we will present a dendritic structure (B) in which the six benzophenone moieties are connected to a central benzene ring in such a way that one of the phenyl rings of each benzophenone is also part of the propeller of the hexaphenylbenzene core (C). The anion radical of B, prepared by electron-transfer quenching with DABCO, showed an intense charge-resonance transition in the near IR region, in addition to the characteristic absorption band at ~750 nm, indicating that a single electron delocalizes via electron transfer over six identical redox-active centers. This conclusion is supported by spectral comparison of the anion radical spectra of a variety of model benzophenone derivatives.

 

New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005