Crown-6-calix[4]arene-capped calix[4]pyrrole: An ion-pair receptor for solvent-separated CsF ions

Jonathan L. Sessler; Sung Kuk Kim; Dustin E. Gross; Chang Hee Lee; Jong Seung Kim; Vincent M. Lynch

doi:10.1021/ja804976f

Crown-6-calix[4]arene-capped calix[4]pyrrole: An ion-pair receptor for solvent-separated CsF ions

Jonathan L. Sessler, Sung Kuk Kim, Dustin E. Gross, Chang Hee Lee, Jong Seung Kim, Vincent M. Lynch

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

142 Citations (Scopus)

Abstract

An ion-pair receptor, 1, containing both cation- and anion-recognizing sites, has been synthesized and characterized. Single-crystal X-ray diffraction structural studies and ¹H NMR spectroscopic analyses confirmed that 1 forms stable 1:1 complexes with CsF in solution and in the solid state in spite of the large separation enforced between the receptor-bound anion and cation. In 9:1 CDCl₃/CD₃OD, binding of fluoride anion within the calix[4]pyrrole core of 1 was not observed in the absence of a cobound cesium cation; however, it was seen in this solvent mixture under conditions where a Cs⁺ cation was bound to the crown ether-strapped calix[4]arene subunit.

Original language	English
Pages (from-to)	13162-13166
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	130
Issue number	39
DOIs	https://doi.org/10.1021/ja804976f
Publication status	Published - 2008 Oct 1

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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AU - Kim, Sung Kuk

AU - Gross, Dustin E.

AU - Lee, Chang Hee

AU - Kim, Jong Seung

AU - Lynch, Vincent M.

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N2 - An ion-pair receptor, 1, containing both cation- and anion-recognizing sites, has been synthesized and characterized. Single-crystal X-ray diffraction structural studies and 1H NMR spectroscopic analyses confirmed that 1 forms stable 1:1 complexes with CsF in solution and in the solid state in spite of the large separation enforced between the receptor-bound anion and cation. In 9:1 CDCl3/CD3OD, binding of fluoride anion within the calix[4]pyrrole core of 1 was not observed in the absence of a cobound cesium cation; however, it was seen in this solvent mixture under conditions where a Cs+ cation was bound to the crown ether-strapped calix[4]arene subunit.

AB - An ion-pair receptor, 1, containing both cation- and anion-recognizing sites, has been synthesized and characterized. Single-crystal X-ray diffraction structural studies and 1H NMR spectroscopic analyses confirmed that 1 forms stable 1:1 complexes with CsF in solution and in the solid state in spite of the large separation enforced between the receptor-bound anion and cation. In 9:1 CDCl3/CD3OD, binding of fluoride anion within the calix[4]pyrrole core of 1 was not observed in the absence of a cobound cesium cation; however, it was seen in this solvent mixture under conditions where a Cs+ cation was bound to the crown ether-strapped calix[4]arene subunit.

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Crown-6-calix[4]arene-capped calix[4]pyrrole: An ion-pair receptor for solvent-separated CsF ions

Abstract

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