||The factors affecting the binding of a series of azo dyes to cyclohexaamylose were determined. All substrates were variously-substituted with a carboxylate group in position-4 and a hydroxy group in position-4'. The carboxylate group has been shown to be capable of penetrating the cyclohexaamylose cavity. Stability is a direct function of the depth of penetration of the dye into the cyclohexaamylose. Higher-order (1 dye: 2 cyclohexaamylose) guest-host interactions have been established in several cases. Mixed solvent studies, water/DMSO, reveal a decrease in complex stabilities relative to the aqueous system alone. The solvent and its hydrophobic interactions with the solutes have been ascertained. Additionally, the dyes have exhibited amphiphilic behavior much like amino acid residues in proteins with regard to their native conformations in solution. The binding interactions have also revealed enthalpy-antropy compensation occurring which is typical of aqueous systems where the solvent is involved as a driving force in the reaction being observed.