Synthesis and Characterization of Hybrid Glycolipids as Functional Organogelators and Hydrogelators.

Abstract

Carbohydrate-based low-molecular-weight gelators are useful and versatile compounds for the preparation of soft materials. Using N-acetyl-d-glucosamine as the starting material, we synthesized and characterized 15 glycolipids containing an amide with different ester functional groups. These include aliphatic derivatives with varying chain lengths and aromatic derivatives. Most of the hybrid amide-esters have molecular weights less than 500 D. These glycolipids were found to be effective gelators for several organic solvents, water, and aqueous solutions. Two efficient hydrogelators were also obtained at low concentrations. A few representative gels were characterized using optical microscopy, atomic force microscopy, and rheology to obtain information on their morphology and gel stability. Three gelators were also used to encapsulate naproxen sodium and toluidine blue. The sustained release of the drug from the gel to the aqueous phase was monitored by UV-vis spectroscopy. These gelators have structural flexibility that can be stimuli responsive. The esters can be hydrolyzed and several gels were converted to solutions under basic conditions. These rationally designed gelators could be utilized as stimuli-responsive smart materials with controlled release properties.