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Abstract: The extent of functional monomer-template complexation in noncovalent molecularly imprinted polymer (MIP) prepolymerization mixtures have been examined using H-1-NMR spectroscopy, and observed complex stabilities have been correlated to polymer-template recognition. The triazine herbicide atrazine was used as a template in molecular imprinting studies using the functional monomers methacrylic acid (MAA), 4-vinyl pyridine (4-VP), and an equimolar mixture of the two. Nuclear magnetic resonance (NMR) titration studies using acetic acid, an analogue for MAA, yielded an average apparent dissociation constant (app K-diss) of 65 +/- 7 mM for atrazine complexation in chloroform (293 K). Studies using pyridine, an analogue for 4-VP, demonstrated no significant complex formation over the concentration range studied. Atrazine MIPs, and corresponding nonimprinted reference polymers, were synthesized using MAA, 4-VP, or an equimolar mixture of the two., and were evaluated using high-performance liquid chromatography (HPLC) and radio ligand binding studies. Importantly, the recognition characteristics of the polymers reflected the observed complex stabilities in the prepolymerization mixtures; thus, MAA MIPs displayed superior recognition and binding capacity compared to polymers prepared with 4-VP. MIPs synthesized using a combination of MAA and 4-VP demonstrated intermediate recognition. These results suggest that NMR spectroscopy may be used as a predictive tool for the screening of functional monomers for use in molecular imprinting protocols
Template and target information: atrazine
Author keywords: Molecularly imprinted polymers, atrazine, monomer complexation, template