Lipophilic calix[4]resorcinarene with phosphorous acid amide groups linking oxygen atoms is a rigid system of the cavitand type, in which conformational flexibility is strongly limited. These chiral receptors form stable Langmuir monolayers on water surface with surface area per molecule in the compressed layer being almost ph-independent.
The surface potential of these compounds is distinctly higher in the presence of substituents and its further increase upon decreasing the pH of the subphase is observed only for the derivatized calixarenes. This means that protonation on the amine centers is the factor determining the properties of the monolayer.
Two chiral, lipophilic calix[4]resorcinarenes of Mannich-base type, containing (S((-)-phenylethylamine (CAL11-PhEt), and (1R,2S)(-)-norephedrine (CAL11-EPh) form Langmuir monolayers on water surface. Chiral discrimination of amino acids: alanine, valine, leucine and tryptophan was observed by the changes in the surface area, which was different for D- and L-forms.
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