Tripodal receptors for the transmembrane transport of anions

Many new synthetic anion receptors are continuously being developed. However, only a limited number of these hosts have been evaluated for their ability to transport anions across lipid bilayers, due to a specific requirement for an ionophore to function. Tripodal scaffolds such as Triethylphenylene (TEP) and Tris(2-aminoethyl)amine (TREN), originally designed for ion recognition, are now well established as efficient transmembrane anion transporters. Building on this foundation, this thesis reports synthetic optimization already known tripodal shaped compounds and synthesis of new tripodal anion receptors with the aim of improving both anion transport efficiency and deliverability to the liposome membrane. The transmembrane transport activity was evaluated with Cl−, PhHPO4−, SO42−, and H2PO4− anions using Large Unilamellar Vesicles (LUVs) as model systems. The efflux of anions was monitored by fluorescence and 31P-NMR assays. In addition, the binding affinities were assessed via NMR titration studies to evaluate performance of the receptors.