| Liquid crystals possess both order and mobility. Hydrated, natural and synthetic amphiphiles self-organize to form various liquid crystal phases as a function of molecular structure, temperature, concentration, and pressure. Self-organization is the ordering of molecules via non-covalent interactions, i.e. hydrogen bonding, van der Waals, π-π interactions, ionic interactions, hydrophobic short-range forces, and London dispersion forces. Amphiphiles contain both polar and non-polar moieties. In general, amphiphiles are composed of a polar, hydrophilic headgroup and one or more non-polar, hydrophobic tail(s). At equilibrium, the unfavorable enthalpic interaction of the polar water molecules with the non-polar amphiphile tails is minimized by the aggregation of the latter with the non-polar tails of other amphiphiles to form a water excluded hydrophobic block, while the hydrophilic headgroups line the interface of the phase-separated aqueous domains. Self-supported arrays of self-organized, hydrated amphiphile assemblies include lamellar/vesicles, various normal and inverted cubic phases, and normal and inverted hexagonal phases. The inverted hexagonal (HII) phase can be considered as aqueous columns patterned in a hexagonal fashion. The polar amphiphile headgroups are well ordered at the water-amphiphile interface, while their non-polar tails are disordered and fill the area between the aqueous water channels. In general, amphiphiles with two or more non-polar chains and a small, poorly hydrated headgroup favor the formation of the HII phase. Longer tails or the incorporation of bulky design elements, i.e. cis-double bonds or branching substituents, in the amphiphile tail(s) lowers the temperature associated with the formation of the HII phase.; Several HII-forming amphiphiles have been designed and synthesized. Upon hydration, the phase behavior of these amphiphiles was evaluated by 31P-NMR assembly characterization. Radical polymerizations were used to stabilize the HII phase assemblies resulting in cross-linked polymer networks. The cross-linked materials displayed dramatically different physical properties, i.e. lowered solubility in common organic solvents. The polymer assembly phase behavior was evaluated via 31P-NMR after polymerization.; A synthetic route to phosphoethanolamines via a novel di-protected glycerophosphoethanolamine has been designed and developed. A phosphoethanolamine lipid has been synthesized using this route. The route appears to be general to the synthesis of any phosphoethanolamine. |
