Dummy Template-Imprinted Polymers for Bisphenol A Prepared Using a Schiff Base-Type Template Molecule with Post-Imprinting Oxidation

A new dummy template molecule, N,N′-bis(3-vinylbenzylidene)-4,4′-diaminodiphenylmethane (VB-DADPM) was designed to synthesize dummy template-imprinted polymer (DIP) for Bisphenol A (BPA). Since the Schiff-base part of VB-DADPM is easily cleaved by a weak acid treatment, the DADPM moiety can be removed after the co-polymerization with cross-linkers. After the post-imprinting oxidation was carried out to transform the residual aldehyde to carboxylic acid, binding sites toward BPA were generated only inside the binding cavity, which had an estimated binding constant of 1.3 × 106 M−1, and could recognize the difference between similar molecules BPA and BPB, the latter of which has an ethyl group instead of a methyl group at the central part of BPA.

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