The stability of the homogenous aggregates formed in H2O:EtOH 19:1 at 2.78 mM of 1 -5 were then determined through zeta potential studies (Table ). The thiourea based self-associated aggregates were found to be the least stable with zeta potential measurements of -56 mV. Substituting the thiourea for the squaramide residue increased the stability of those nanostructures formed, with zeta potential measurements of -79 mV and -73 mV reported for 4 and 5 respectively. We believe that this is due to the increased strength of SSA anion dimerization events (2 Kdim = 105 M -1 and 5 Kdim = 7636 M -1 ). Although 3 does not contain a squaramide residue and has a much lower self-associative binding constant of 2.7 M -1 in DMSO-d6 0.5% H2O, the enhanced stability provided by the planar, hydrophobic benzothiazole functionality gives rise to aggregates with a zeta potential of -86 mV. Tensiometry experiments, the results of which are summarised in Table , confirmed 1 -5 to exhibit surfactant properties in a H2O:EtOH 19:1 solution, as surface tension is lowered upon increasing concentrations of SSAs, however the critical aggregation concentration (CAC) could only be determined for 1 and 3 due to SSA solubility.