Self-Organization of Carbohydrate-Derived Amphiphilic Compounds: Insights into Their Supramolecular Assembly

This study describes the synthesis and self-assembly properties of two sugar-derived surfactants constructed by click reaction from readily accessible building blocks. After structural characterization, their self-assembly processes were studied in two biocompatible solvents, isopropyl myristate and methyl laurate, as well as in toluene. Detailed experiments by dynamic light scattering (DLS) and small-angle X-ray scattering (SAXS) confirmed the formation of reverse micelles (RMs). The findings reveal the formation of spherical aggregates with low polydispersity indices, indicating a high degree of size uniformity. SAXS analysis further demonstrated that these aggregates possess a smooth and well-defined RMs-nonpolar solvent interface. Notably, the system in toluene as the non-polar phase exhibited a unique behavior, suggesting distinct structural characteristics that differ from those observed in the biocompatible solvents. A low-resolution structural model revealed that the aggregates contain an internal gap compatible with a reverse vesicle consisting of a bilayer of amphiphile with the hydrophilic heads pointing towards the interior and the exterior of the bilayer with toluene on both sides of the bilayer. In summary, this study explores the self-assembly characteristics of sugar-based surfactants in non-polar environments that mimic biological membranes. The findings highlight the significant potential of these surfactants in supramolecular chemistry and glycobiology.