Bipyrrole-strapped calix[4]pyrroles: Strong anion receptors that extract the sulfate anion

Sung Kuk Kim; Juhoon Lee; Neil J. Williams; Vincent M. Lynch; Benjamin P. Hay; Bruce A. Moyer; Jonathan L. Sessler

doi:10.1021/ja5086996

Bipyrrole-strapped calix[4]pyrroles: Strong anion receptors that extract the sulfate anion

Sung Kuk Kim, Juhoon Lee, Neil J. Williams, Vincent M. Lynch, Benjamin P. Hay, Bruce A. Moyer, Jonathan L. Sessler

Chemical Separations Group

Research output: Contribution to journal › Article › peer-review

84 Scopus citations

Abstract

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_8-10)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).

Original language	English
Pages (from-to)	15079-15085
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	136
Issue number	42
DOIs	https://doi.org/10.1021/ja5086996
State	Published - Oct 22 2014

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title = "Bipyrrole-strapped calix[4]pyrroles: Strong anion receptors that extract the sulfate anion",

abstract = "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(C8-10)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).",

author = "Kim, {Sung Kuk} and Juhoon Lee and Williams, {Neil J.} and Lynch, {Vincent M.} and Hay, {Benjamin P.} and Moyer, {Bruce A.} and Sessler, {Jonathan L.}",

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T2 - Strong anion receptors that extract the sulfate anion

AU - Kim, Sung Kuk

AU - Lee, Juhoon

AU - Williams, Neil J.

AU - Lynch, Vincent M.

AU - Hay, Benjamin P.

AU - Moyer, Bruce A.

AU - Sessler, Jonathan L.

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AB - 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(C8-10)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).

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Bipyrrole-strapped calix[4]pyrroles: Strong anion receptors that extract the sulfate anion

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