Supramolecular Hydrogels Based on Glycoamphiphiles: Effect of the Disaccharide Polar Head

Supramolecular hydrogelators based on amphiphilic glycolipids have been prepared by clicking different sugar polar heads to a hydrophobic linear chain by copper(I)-catalyzed azide–alkyne [3 + 2] cycloaddition. The influence of the sugar polar head on the gelation properties in water has been studied, and the liquid crystalline properties of the amphiphilic materials have also been characterized. Stable hydrogels at room temperature have been obtained and the fibrillar supramolecular structures formed by the self-assembly have been studied by different microscopic techniques on the dried gel (xerogel) and hydrated conditions in order to characterize the micro- and nanostructures. Self-assembly gives rise to supramolecular ribbons with a torsion that is related to a chiral supramolecular arrangement of amphiphiles. The formation of an opposite helical arrangement of the ribbons has been found to depend on the sugar polar head. This fact was confirmed by circular dichroism (CD).