ABSTRACT
A set of amphiphilic glycolipids were synthesized from cardanol (a by-product of cashew industry) and diaminopyridine (DAP). These amphiphiles encompass self-assembling units such as long hydrophobic saturated or unsaturated chain, open or closed sugar as headgroup and aromatic (phenyl or DAP) as linker. Amphiphiles from both series (cardanyl and DAP) exhibited excellent self-assembling properties to produce various lipid based materials ranging from structurally unordered fibers to highly uniform nanotubes. Their self-assembling properties were investigated by various techniques including EF-TEM, SEM, XRD and DSC. The nanotubes are comprised of bilayer structure with interdigitated alkyl chains associated through hydrophobic interactions, hydrogen bonding and π-π stacking. The self-assembling behavior of cardanyl glucosides and the synthetic analogues from diaminopyridine were compared. The tubes derived from DAP amphiphiles contain accessible 2,6-diaminopyridine linker that can interact with thymidine and related nucleosides through multipoint hydrogen bonding, thereby quenching the intrinsic fluorescence of the aromatic linker. These results clearly showed that efficient molecular design, and synthesis of novel amphiphiles from renewable resources will lead to supramolecular nanostructures and nanomaterials, otherwise under-utilised.
