The synthesis and preliminary solution phase ion binding properties of the N-tosylpyrrolidine calixpyrrole 2 are reported. This β-octaalkyl-substituted calixpyrrole, the first to be prepared via a direct condensation reaction, was obtained by reacting the 3,4-alkyl-functionalized pyrrole 8 with acetone in the presence of an acid catalyst. On the basis of 1H NMR spectroscopic analyses and isothermal titration calorimetry, it was concluded that, compared with the parent, β-unsubstituted calixpyrrole ( 1), compound 2 possesses significantly enhanced binding ability for halide anions in chloroform.
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Furthermore, 2 proved capable of solubilizing in chloroform solution the otherwise insoluble salts, CsF and CsCl. These effects are ascribed to the interactions between the four tosyl groups present in 2 and the counter cations of the halide anion salts. Learn more about these metrics Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days. The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online.
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