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

Carbohydrate based low molecular weight gelators (LMWGs) are useful and versatile compounds for the preparation of soft materials. Using N-acetyl D-glucosamine as the starting material, fifteen glycolipids containing an amide with different ester functional groups were synthesized and characterized. 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 their morphology and gel stability. Three gelators were also used to encapsulate naproxen sodium and toluidine blue. The sustained release of the drug from gel to aqueous phase was monitored by UV-vis spectroscopy. These gelators have structure flexibility that can be stimuli-responsive under a basic environment. The esters can be hydrolyzed and the gels were converted to solutions under basic conditions. These rationally designed gelators could be utilized as stimuli-responsive smart materials with controlled release properties.