N-Tosylpyrrolidine calix[4]pyrrole: synthesis and ion binding studies |
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Authors: | Kim Sung Kuk Gross Dustin E Cho Dong-Gyu Lynch Vincent M Sessler Jonathan L |
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Affiliation: | Department of Chemistry and Biochemistry, 1 University Station-A5300, The University of Texas at Austin, Austin, Texas 78712-0165, USA. |
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Abstract: | The synthesis and preliminary solution phase ion binding properties of the N-tosylpyrrolidine calix[4]pyrrole 2 are reported. This β-octaalkyl-substituted calix[4]pyrrole, 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 (1)H NMR spectroscopic analyses and isothermal titration calorimetry, it was concluded that, compared with the parent, β-unsubstituted calix[4]pyrrole (1), compound 2 possesses significantly enhanced binding ability for halide anions in chloroform. 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. |
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