Exploiting β-cyclodextrin as functional monomer in molecular imprinting for achieving recognition in aqueous media

A series of molecularly imprinted polymers (MIPs) for 4,4'-(1.4-phenylenediisopropylidene)bisphenol (BPP) were prepared by using beta-cycloclextrin (beta-CD) as functional monomer, toluene 2,4-diisocyanate (TDI) or 4,4'-Diphenylmethane diisocyanate (DDI) as the cross-linker. The results of binding experiments showed that the MIPs can bind the template selectively in aqueous media. The binding specificity mechanism of the polymers was investigated in detail. The template molecule is too large and cannot be included in the cavity of one beta-CD molecule. The mutual orientation of beta-CD molecules in the imprinted polymers is regulated by molecular imprinting, so that they can cooperatively bind the template molecule. It is suggested that the major contribution to the recognition ability of the imprinted polymer was the stereo-shape effect inherent in the MIPs. The study indicated that hydrophobic effects play an important role in the recognition process. (c) 2008 Elsevier B.V. All rights reserved.