Symbiotic Supramolecular self-association and the effects on antimicrobial activity

In this research the self-assembly and self-association processes occurring between supramolecular aggregates and surfactant structures were studied. Three amphiphilic molecules have been presented in this thesis. Two of which are novel and one which has been previously synthesised and characterised. The characterisation, self-association, binding modes and antimicrobial activity of these amphiphiles have been explored and reported. These amphiphiles containing tetrabutylammonium (TBA) countercation and anionic hydrogen bond donor/hydrogen bond acceptor unit have been observed in the solid, solution and gas states using a combination of scientific techniques. Observing these molecules in different solvent systems (DMSO and EtOH: H2O (1:19) and at various concentrations has shown the ability of the anionic monomer to self-associate in solution, thus resulting in the formation of dimeric (in DMSO) and extended aggregate species (in EtOH/H2O). A series of three mixture combinations containing the compounds were also studied. In addition, these mixtures of these amphiphilic salts showed their ability to self-sort which resulted in the increase of their antimicrobial activity and decrease in critical micelle concentration

A Symbiotic Supramolecular Approach to the Design of Novel Amphiphiles with Antibacterial Properties Against MSRA

Herein, we identify Supramolecular Self-associating Amphiphiles (SSAs) as a novel class of antibacterials with activity towards Methicillin-resistant Staphylococcus aureus. Structure-activity relationships have been identified in the solid, solution and gas phases. Finally, we show that when supplied in combination, SSAs exhibit increased antibacterial efficacy against these clinically relevant microbes

Ionicity-dependent proton-coupled electron transfer of supramolecular self-assembled electroactive heterocycles

Herein, we investigate the electrochemical properties of a class of Supramolecular Self-associated Amphiphilic salts (SSAs). We show that varying ionic strength of an SSA solution can cause a switching of the thermodynamics and kinetics of electron transfer. The effect of self-assembly on proton-coupled electron transfer has implications for the understanding of electron transfer kinetics in aqueous organic redox flow batteries, especially at high concentration where organic–organic intermolecular interactions become dominant even for highly soluble organic species

Towards the prediction of global solution state properties for hydrogen bonded, self-associating amphiphiles

Through this extensive structure-property study we show that critical micelle concentration correlates with self-associative hydrogen bond complex formation constant, when combined with outputs from low level, widely accessible, computational models. Herein, we bring together a series of 39 structurally related molecules obtained through stepwise variation of a hydrogen bond donor-acceptor amphiphilic salt. The self-associative and corresponding global properties for this family of compounds have been studied in the gas, solid and solution states. Within the solution state we have shown the type of self-associated structure present to be solvent dependent. In DMSO, this class of compound show a preference for hydrogen bonded dimer formation, however moving into aqueous solutions the same compounds are found to form larger self-associated aggregates. This observation has allowed us the unique opportunity to investigate and begin to predict selfassociation events at both the molecular and extended aggregate level