Saccharide imprinting of poly(aniline boronic acid) in the presence of fluoride

A new approach for the electrosynthesis of saccharide-imprinted poly(aniline boronic acid) is described. The method involves the formation of a saccharide-aminophenylboronic acid complex in the presence of fluoride to allow the electropolymerization of a self-doped, molecularly imprinted polyaniline. The formation of the anionic monomer complex enables electrochemical polymerization at near neutral pH (5-7) ensuring the incorporation of saccharide in the resulting, self-doped polymer. In this work, films were imprinted with D-fructose where saccharide-aminophenylboronic acid complexation occurred in the presence of one equivalent of fluoride. The selectivity toward D-fructose relative to D-glucose showed an increase of over 25% as a result of imprinting. In addition to the enhanced selectivity, to the best of our knowledge this is the first example of the electropolymerization of a self-doped polyaniline homopolymer under neutral pH conditions.