Imprinted polymeric materials. Insight into the nature of prepolymerization complexes of quercetin imprinted polymers.

ABSTRACT

Molecular imprinting techniques have proved to be a highly accessible method for producing molecule-specific recognition materials for a variety of applications, ranging from sensing to catalysis and separations. In noncovalent imprinting, it is anticipated that polymerizable complexes are created in the prepolymerization solution via self-assembly of functional monomers and template molecules resulting from inherent chemical complementarity, which will ideally form binding sites within the cross-linked matrix after polymerization. On the basis of 1H NMR data and X-ray crystallographic evidence, we now infer a more important role for template self-association for the recognition properties of quercetin-imprinted polymers. While directly applicable to fundamental understanding of the molecular imprinting mechanism of this polyphenol, on a more generic scale, this work also demonstrates the utility of this strategy toward analyzing complex noncovalent interaction mechanisms between small molecules. These interactions are of particular interest for quercetin and other members of the flavone/flavonoid class of compounds, which are radical-scavenging polyphenols of substantial interest to biomedicine.