Submitted to: Journal of Organic Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/10/2011
Publication Date: 2/24/2011
Citation: Wang, G., Yang, H., Cheuk, S.Y., Coleman, S. 2011. Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators. Journal of Organic Chemistry. 7:234-242. Interpretive Summary: Carbohydrates are an abundant and renewable natural resource, which makes them ideal starting materials in organic synthesis. This research transforms D-glucose, the most abundant monosaccharide, into low molecular weight gelators. Unlike polymer gelators, this class of compounds form a linear chain network, using intermolecular interactions in a phenomenon known as self-assembly. After gentle heating or sonication, these molecules can form gels at concentrations of 0.1% by weight, well below their polymeric counterparts. Previous research has looked at various changes to the core structure, and side chains to discern any relationship between structure and gelation ability. This study takes that relationship one step further by observing the affect of the anomeric oxygen.
Technical Abstract: Low molecular weight gelators are an important class of molecules. The supramolecular gels formed by carbohydrate derived low molecular weight gelators, are interesting soft materials that show great potential for many applications. Previously, we synthesized a series of methyl 4,6-O-benzylidene-a-D-glucopyranoside derivatives; and found that several of them are good gelators for water, aqueous mixtures of DMSO, or aqueous mixtures of ethanol. The gelation efficiency of these glycolipid derivatives is dependent upon the structures of their acyl chains. In order to understand the influence of the anomeric position of the sugar headgroup towards self-assembly, we synthesized a series of 1-deoxyglucose analogs, and examined their gelation properties in several solvents. Several long chain esters, including diacetylene containing esters, and aryl esters; exhibited gelation in ethanol, aqueous ethanol, or aqueous DMSO. The synthesis and characterization of these novel analogs are reported.