Carbohydrate derived molecular gelators are interesting compounds with numerous applications. Previously, we have shown that certain per-acetylated D-glucosamine and D-glucose based triazole derivatives are low molecular weight hydrogelators and organogelators. They were synthesized by copper catalyzed sugar azide and alkyne cycloadditions. Among the five-membered ring heterocycles, besides triazoles, isoxazoles can also contribute to favorable intermolecular interactions that result in effective self-assembled molecular network and gel formation.  In order to discover novel sugar based low molecular weight gelators, we synthesized a new series of sugar derivatives containing 3,5-disubstituted isoxazole functional groups. D-glucosamine and glucose derived propargyl glycosides were coupled with a series of α-chloro-aldehyde oximes, which were prepared from the corresponding aldehyde. These glycoconjugates were analyzed for gelation properties in organic solvents and aqueous solutions. A majority of the compounds were found to be effective gelators for aqueous mixtures of ethanol and dimethyl sulfoxide. Several compounds were able to form hydrogels at concentrations of 0.2-2.0 wt%. The structures of the aldehydes and the sugars are important for the gelation properties. One hydrogelator was studied for dye absorption and it was able to remove toluidine blue dye from aqueous mixtures. In this presentation, the synthesis and gelation properties of different analogs and the applications of these compounds for environmental applications, possible applications as ligands for catalysis will be presented.

Synthesis of isoxazole containing glycoconjugates and the study of their self-assembling properties

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