We have investigated the self-associative properties of five structurally diverse, but related SSAs, 1 -5. We have shown that the introduction of the squaramide functionality increases the strength of SSA anion hydrogen bonded self-association events by an order of magnitude or more in comparison to the thio(urea) analogues within a DMSO-d6 0.5 % H2O solution. We have also co-formulated 1 -5 in a 1:1 ratio to produce a -j. We have shown that changing the structure of these SSAs as well as co-formulation can be used to modulate the selfassociating properties of these systems, and the properties of any aggregate formed in a 19:1 H2O:EtOH solution.