Bioorganic & Medicinal Chemistry 2007-09-15

Retention behavior of phenoxyacetic herbicides on a molecularly imprinted polymer with phenoxyacetic acid as a dummy template molecule.

Huiting Zhang, Tao Song, Wei Zhang, Wei Hua, Canping Pan

Index: Bioorg. Med. Chem. 15(18) , 6089-95, (2007)

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Abstract

Molecular imprinted polymers (MIPs) binding with phenoxyacetic acid (PA) as a dummy template molecule were synthesized via thermal initiation in aqueous medium. The retention behaviors of benzoic acid (BA), PA, 2-methyl-4-chlorophenoxyacetic acid (MCPA), 4-chlorophenoxyacetic acid (4-CPA), and 2,4-dichlorophenoxyacetic acid (2,4-D) on this MIP column indicate that this material can selectively retain phenoxyacetic herbicides. To investigate these recognition mechanisms, the interactions between the functional monomer 4-vinylpyridine (4-VP) and PA or 2,4-D were investigated by computational modeling. (1)H NMR spectroscopy of 2,4-D titrated by 4-VP was recorded. The chemical shift of the 2,4-D acidic proton (12.15-14.32ppm) shows the existence of the ion-pair interaction. This kind of polymers could be useful as stationary phases to extract 2,4-D, 4-CPA or MCPA and avoid leakage of a trace amount of target analyte remaining in the MIPs.