The work presented focuses on the study of the permeability of the phospholipid bilayer membranes of liposomes---a model of biological membranes---by the use of carrier molecules as well as on the study of the permeability of polymer nanocapsules when using liposomes as a template for their synthesis. The results of this work can lead to the development of novel biomedical devices and to the development of novel classes of polymer nanomaterials.; A series of carrier molecules, alpha-aminophosphonates, was synthesized in order to transport a polar molecule, an amino acid (alanine), across the lipid bilayer of synthetic liposomal membranes. Aminophosphonates were prepared by the Kabachnik-Fields reaction from a primary amine, a phosphite, and a carbonyl compound. Transport of alanine, a model polar molecule, was studied by liposome efflux experiments coupled with enzymatic assays. All carriers exhibited moderate transport properties, which makes them suitable for construction of controlled released devices.; A second project involved the use of liposomes as a template for the synthesis of polymer nanocapsules. Porous polymer nanocapsules were prepared by co-dissolving hydrophobic monomers and porogens in the interior of bilayer membranes followed by polymerization and subsequent removal of lipid scaffold and porogens. Structural characterization was performed by electron microscopy. Permeability of polymer nanocapsules was studied by analyzing the retention of molecules of various sizes in the capsule interior. Selective pores were produced that were capable of differentiating molecules with a relatively small size difference. This work describes a new class of polymer nanomaterials previously unavailable.
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