N-Tosylpyrrolidine Calix[4]pyrrole: Synthesis and Ion Binding Studies

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• 作者：Sung Kuk Kim ; Dustin E. Gross ; Dong-Gyu Cho ; Vincent M. Lynch ; Jonathan L. Sessler
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：February 18, 2011
• 年：2011
• 卷：76
• 期：4
• 页码：1005-1012
• 全文大小：1033K
• 年卷期：v.76,no.4(February 18, 2011)
• ISSN：1520-6904

文摘

The synthesis and preliminary solution phase ion binding properties of the N-tosylpyrrolidine calix[4]pyrrole 2 are reported. This 尾-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 ¹H NMR spectroscopic analyses and isothermal titration calorimetry, it was concluded that, compared with the parent, 尾-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.