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Bipyrrole-strapped calix[4]pyrroles: Strong Anion Receptors That Extract the Sulfate Anion

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

J Am Chem Soc. 2014 Oct 22;136(42):15079-85.

PMID: 25254498

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).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP14190160	Tetramethylammonium sulfate		14190-16-0	Price

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