Abstract
Water-soluble p -sulfonatocalix[7]arene 1 has been synthesized in good yield through standard procedures and its conformational preferences have been investigated by Monte Carlo conformational searches. The acid–base properties of 1 were investigated by means of potentiometric titration, obtaining p K a values in agreement with those reported for other p -sulfonatocalix[ n ]arene homologs. The binding ability of 1 toward organic quaternary ammonium cations such as Diquat ( 2 ), Paraquat ( 3 ), and Chlormequat ( 4 ) was investigated by means of 1 H NMR titrations in D 2 O at pD=7.3, DOSY NMR measurements, and 2D ROESY NMR spectroscopy. Spectrofluorimetry proved to be a useful method for the determination of trace amounts of 2 and 3 in aqueous solution by using Acridine Orange bound to 1 as a chemical indicator.
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