Modulation of the reactivity of benzophenones in the different binding sites of bile salt aggregates

ORGN 588

Cornelia Bohne, Chelsea Wozniak, and Oscar Waissbluth. Department of Chemistry, Univeristy of Victoria, PO Box 3065, Victoria, BC V8W 3V6, Canada
Bile salts are complex supramolecular structures, which provide binding sites with different properties for small guest molecules. The reactivity of triplet excited benzophenone derivatives within these aggregates was studied to obtain information on how the structure of the bile salt aggregates affects the reactivity of the excited states. In the confined and hydrophobic primary aggregates most of the triplet benzophenones react by hydrogen abstraction. The dynamics of binding to the secondary aggregate is much faster and self-quenching of triplet benzophenone competes with the exit of the excited state to the aqueous phase. The reactivity of the excited ketones is influenced by the hydrophobicity of the benzophenones and the different structures of the bile salt monomers.