Considerable research activity is now in progress to use renewable carbon from biorefinery process streams for the production of new chemicals and materials. Carbohydrates being the primary process stream within the biorefinery can be sources of many novel, biologically important chemicals and materials. The diversity of substitution patterns, stereochemistry and chirality in carbohydrates offer challenges in developing a wide range of useful and selective methods for synthetic modification.

Glycals, which are carbohydrates with a double bond between carbons 1 and 2, provide scaffolds for a wide range of structural modification in addition to enhanced reactivity and versatility of these materials for construction of new nanoscale materials. We have synthesized a family of glycal based bolaamphiphiles by linking two glycal headgroups with a long, nonpolar hydrocarbon chain. These compounds exhibit diversity in head group structure, well-defined reactive sites as a result of the unique chiral centers and provide potential for π-stacking through the double bond. Upon dispersion in aqueous solution, these bolaforms undergo self-assembly to form new nanostructural materials. We will report our effort to synthesize a library of glycal based bolaforms by chemical modifications incorporating a wide range of head groups and varying hydrophobic spacer length. The effect of structural modification on the ultimate structure adopted by the supramolecular array will also be discussed. Eventually, structural analysis and modeling to convert bolaform library to macromolecular assemblies and develop a predictive model of how structural changes at molecular level are reflected at macromolecular level will be attempted.