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

作者：Kim Sung Kuk; Gross Dustin E; Cho Dong Gyu; Lynch Vincent M; Sessler Jonathan L^*

来源：Journal of Organic Chemistry, 2011, 76(4): 1005-1012.

DOI：10.1021/jo101882r

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

• 出版日期2011-2-18