Harnessing non-covalent interactions in molecular traps for probable human carcinogen butylated hydroxyanisole

Abstract

We report the synthesis, characterization and performance evaluation of nine molecularly imprinted polymers (MIPs) for butylated hydroxyanisole (BHA), a common antioxidant used in the food industry but is carcinogenic at high concentrations. Vinyl-functionalized imidazole and pyridine monomers were thermally cured with BHA as template, ethylene glycol dimethacrylate as cross-linker, and 1,1ʹ-azobis(cyanohexane carbonitrile) as initiator. The molar ratio of two functional monomer combinations, which can be 1-vinylimidazole (1-VI), 2-vinylpyridine (2-VP) or 4-vinylpyridine (4-VP), was varied and the polymer was cured at 60°C for 36h. Spectrophotometric batch-binding analyses of BHA showed that the optimum uptake was observed for 1-VI- and 4-VP-based MIPs, with a maximum binding capacity of 6.078mg BHA per gram MIP. The observed performance was rationalized by the non-covalent interactions between the template and the functional monomers.