Anionic Glucophospholipids—A New Family of Tubule‐Forming Amphiphiles

Abstract

Abstract:A new family of amphiphiles that form tubules (i.e.. hollow cylindrical bilayer-based microstructures) by selfaggregation has been identified, namely, anionic glucophospholipids of type 1, in which a double-tailed hydrophobe is grafted through a phosphate linkage to the 0-6 position of a polar glucose head group. Compounds 1 a-c self-assemble into stable, hollow tubular microstructures when dispersed in water and cooled below the temperature at which the transition between crystal and liquid-crystal phases takes place (estimated from change in turbidity). The diameter of the microstructures appears to depend on the nature of the hydrophobic tail, significantly smaller diameters being obtained for fluorinated tails. No tubules were obtained when galactose (2a-c, pH < 11) or mannose (3a-c) derivatives were used instead of glucose derivatives. or when glucose was derivatized at the 0-3 (4b) rather than 0-6 position; in these cases only vesicles were formed. Tubules made of 1 converted rapidly into giant vesicles when

Small-Angle Scattering and Electron Microscopy Investigation of Nanotubules Made from a Perfluoroalkylated Glucophospholipid

“…F-Glu (35 mM, 3% w/v) was hydrated for 30 min at 60°C, i.e., above its phase transition temperature (12) and was dispersed in water by sonication for 2 min at 60°C. The pH of the dispersion was measured to be 7.…”

“…These vesicles are significantly more stable than those obtained from hydrogenated analogs. Some F-amphiphiles, including dimorpholinophosphates and glucophospholipids, were found to form not only vesicles but also stable hollow bilayer-based micro-and nanotubules (11,12). The transition from vesicles to such tubules was documented, but no analysis of the structure of the latter assemblies has been carried out yet.…”

The Incorporation of Indigo Molecules in Sepiolite Tunnels

“…The encapsulating tubular systems originate from fluorinated organic, [7,8] hydrogenated organic, [9,10] mineral, organometallic or sol-gel materials. They are synthesised in the same way as organic tubules, sol-gel mesoporous materials, self-assembled complex architectures, [11] zeolite L, [12] carbon nanotubes [13] or metal disulfide nanotubes.…”

Chiral Molecular Self‐Assembly

“…48,49 Both the hydrogenated (12) and partially fluorinated (13) amphiphiles were found to form tubular microstructures when dispersed in water. No tubules were seen in galactose or mannose derivatives.…”