Water-compatible molecularly imprinted polymers (MIPs) for caffeine were synthesized in aqueous medium with a new functional monomer, 1-(α-methyl acrylate)-3-methylimidazolium bromide (1-MA-3MI-Br), which had π–π and hydrogen-bonding interactions. Caffeine-imprinted polymers were prepared in suspension polymerization with 1-MA-3MI-Br and methacrylic acid (MAA), which only had hydrogen bonding, as a functional monomer. For the specific binding characteristics of the new functional monomer 1-MA-3MI-Br, the adsorption capacity and relative separation factor (β) of MIPs for caffeine were significantly enhanced. The maximum adsorption capacities of 1-MA-3MI-Br–MIP and MAA–MIP imprinted microspheres for caffeine were 53.80 and 28.90 μmol/g, respectively. Moreover, the relative separation factors were measured by comparison of the separation characteristics under competitive adsorption conditions. The results showed that the β of MAA–MIP for caffeine relative to theophylline was only 1.65; this showed a very poor recognition selectivity for caffeine, but β of 1-MA-3MI-Br–MIP for caffeine with respect to theophylline was remarkably enhanced to 3.19; this showed an excellent recognition selectivity and binding affinity toward caffeine molecules in an aqueous environment. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013
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