The properties of amphiphilic calix[4]arenes and thiacalix[4]arenes containing the same polar N-tetrahydroxyethylimidazolium groups on one side and alkyl fragments on the other side of the macrocyclic platform are shown. Critical aggregation concentration (CAC) values were studied with three methods: solubilization of Orange OT (a); binding of pyrene (b); interaction with eosin Y (c). Absorbance and emission plots of interaction with eosin Y were effectively calculated by a sigmoidal Boltzmann type function. Different solubilizing ability, interaction with a dianion dye, and selectivity of the of binary system macrocycle-eosin Y respectively to adenosine phosphates (mono-, di-or triphosphate) are shown.