Novel bolaamphiphiles with saccharide polar headgroups: synthesis and supramolecular self-assembilies

Two series of novel sugar-based bolaamphiphiles characterized by a tetraether-type aliphatic linker or a linker composed of a single polymethylene chain were synthesized. Evaluation of their self-assembling properties was performed using optical microscopy, freeze fracture electron microscopy and dynamic fight scattering. Unsymmetrical phosphate derivatives spontaneously formed thermostable monolayered vesicles, whereas neutral glycolipids including a cyclopentane ring in the middle of the bridging chain, exhibited unusual two by two monolayer associations. Bipolar surfactants possessing a single polymethylene bridging chain were found to self-organize into bilayered or monolayered vesicles, disks or fibres depending on the symmetrical or unsymmetrical structure of the lipids, the bridging chain length, the nature of the polar groups and also the structure of the spacers. (C) 2003 Society of Chemical Industry.