Binding of carboxylatopillar[5]arene with alkyl and aryl ammonium salts in aqueous medium

Abstract

The complex formation of alkyl ammonium salts by water-soluble carboxylatopillar[5]arene (CP5A) in aqueous medium is reported. p-Xylene diammonium salt and a series of secondary alkyl ammonium salts with various alkyl groups have been prepared and investigated for complex formation. All the ammonium salts exhibit strong host–guest complexation with CP5A under neutral aqueous conditions. 1H NMR, 1H DOSY and 2D NOESY NMR experiments have been performed to characterize these inclusion complexes. In this study, the hydrophobic and electrostatic interactions govern the complex formation leading to the formation of pseudorotaxane species. Five pseudo[2]rotaxanes and one pseudo[3]rotaxane were obtained whose association constant values and stoichiometry were evaluated by an NMR titration method. The results indicate the use of ammonium salts as new complimentary synthons for CP5A in aqueous medium, adding to the repertoire of existing recognition motifs such as paraquat and 1,4-bis(pyridinium) derivatives.