Synthesis and gelation property of a series of disaccharide triazole derivatives

Low molecular weight gelators are important for the study of supramolecular chemistry and have useful applications for biomaterials. Glycomimetics that are easily accessible and have useful gelation properties are especially interesting molecules. In this research, nine per-O-acetyl lactosyl- and thirteen per-O-acetyl maltosyl triazole derivatives were synthesized and analyzed. Most of the maltosyl triazoles and one of the lactosyl derivatives were found to be effective molecular gelators. The supramolecular gels were characterized using rheology and optical microscopy and they exhibited morphologies ranging from fibers to planar sheets. The self-assembling properties of selected lactosyl and maltosyl triazole derivatives were studied using 1H NMR spectroscopy at different temperatures. The NMR studies revealed that the triazole moiety in these compounds played an important role in the formation of the supramolecular assembly, but the sugar moiety configurations are more influential towards gelation. Naproxen and chloramphenicol were used as the model drugs to assess the potential of these compounds in drug delivery applications. A pH responsive gelator showed faster delivery of chloramphenicol at mild basic conditions than neutral conditions. The effective disaccharide triazole-based molecular gelators are useful for the preparation of advanced soft materials that have potential applications as matrix for immobilization of drugs or biomolecules. [Display omitted] •Twenty two heptaacetyl maltosyl/lactosyl triazoles have been synthesized.•Many of the maltose-linked triazoles are effective molecular gelators.•The gels could immobilize drug molecules for sustained release.