Preparation of molecularly imprinted polymers: Diethyl(3-methylureido)(phenyl)methylphosphonate as a dummy template for the recognition of its organophosphate pesticide analogs

A novel compound, diethyl(3-methylureido)(phenyl)methylphosphonate (DEP), possessing an organophosphate skeleton, was synthesized and used as a dummy template to prepare molecularly imprinted polymers (MIPs) for the recognition of organophosphate pesticide analogs. Computational modeling was used to study the primary intermolecular interactions in the prepolymerization mixture. It was found that the interaction force between DEP and the monomers was hydrogen bonding. A series of MIPs were synthesized with different monomers and were evaluated by adsorption experiments, which showed that methacrylic acid was used as an appropriate monomer and a molar ratio of DEP to MAA of 1 : 9 was optimal. Scatchard analysis showed that there might have been two types of binding sites in the MIPs. DEP and several pesticides were used in molecular recognition specificity tests of DEPMIP, which exhibited better selectivity and reservation ability for organophosphate pesticides, such as methamidophos and orthene, possessing amino or imino groups and a smaller steric hindrance. On the basis of the use of a dummy molecule as template, the problem of template leakage could be avoided; this, thereby, improved the specificity of analysis. (C) 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012