Recognition properties of receptors based on dimesitylmethane-derived core: di- vs. monosaccharide preference

Dimesitylmethane-derived receptors 12 and 13, incorporating four heterocyclic recognition groups capable of serving as hydrogen bonding sites, were designed to recognize disaccharides. It has been shown by 1H NMR and fluorescence spectroscopic titrations that compounds 12 and 13 display high binding affinities toward alpha- and beta-maltoside, as well as strong di- vs monosaccharide preference in organic media. Both hydrogen-bonding and interactions of the sugar CH's with the phenyl rings of the receptor contribute to the stabilisation of the receptor-sugar complexes, as indicated by experimental data and molecular modeling calculations.