Supramolecular Self-associating Amphiphiles (SSAs)

Abstract

This thesis reports the synthesis of 30 structurally related compounds, related by stepwise variation of a hydrogen bond donor-acceptor amphiphilic salt. The self-associative and corresponding global properties of these compounds were investigated in the solid state, solution state and gas phase to enable elucidation of any structure-activity relationships. In the solution state, it was established that the molecular self-association of these compounds could be controlled through modification of the solvent environment. In organic DMSO these compounds principally form dimeric species and in an aqueous environment, spherical aggregates were preferentially formed. The addition of salt to the aqueous solution resulted in the generation of a hydrogel. The physicochemical properties and antimicrobial properties of these gelated materials were then investigated, where it was shown that these hydrogels exhibit antimicrobial properties against both Gram-negative and Gram-positive bacteria. Finally, a tool-kit of novel high-throughput microplate reader technology was developed to assess the presence of dimers, spherical aggregates or fibres in the solution state.