Bipyrrole-Strapped Calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion

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• 作者：Sung Kuk Kim ; Juhoon Lee ; Neil J. Williams ; Vincent M. Lynch ; Benjamin P. Hay ; Bruce A. Moyer ; Jonathan L. Sessler
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：October 22, 2014
• 年：2014
• 卷：136
• 期：42
• 页码：15079-15085
• 全文大小：386K
• ISSN：1520-5126

文摘

Cage-type calix[4]pyrroles 2 and 3 bearing two additional pyrrole groups on the strap have been synthesized. Compared with the parent calix[4]pyrrole (1), they were found to exhibit remarkably enhanced affinities for anions, including the sulfate anion (TBA⁺ salts), in organic media (CD₂Cl₂). This increase is ascribed to participation of the bipyrrole units in anion binding. Receptors 2 and 3 extract the hydrophilic sulfate anion (as the methyltrialkyl(C_8鈥?0)ammonium (A336⁺) salt) from aqueous media into a chloroform phase with significantly improved efficiency (>10-fold relative to calix[4]pyrrole 1). These two receptors also solubilize into chloroform the otherwise insoluble sulfate salt, (TMA)₂SO₄ (tetramethylammonium sulfate).