Six hydrophobic p-tert-butylcalix [4]arenes bearing at the lower rim two bipyridyl moieties and two alkyl or alkylaryl moieties or free hydroxyl groups in alternate positions were synthesized. The behavior of these molecules in Langmuir films was studied using surface pressure (Π) and surface potential (∆V) measurements performed as a function of film compression (compression isotherms) or as a function of time. For chosen calixarenes, Brewster angle microscopy in monolayers was utilized. The results obtained revealed that the calixarene lateral nonbipyridyl groups, different for each molecule, determined the intermolecular interactions in monolayers. On the contrary, since no significant differences could be observed in calixarene conformational reorganization, it was concluded that the bipyridyl groups, common for all molecules, dominated this process. Molecular mechanics simulations using HyperChem have supported the above interpretations.
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