Controlling cesium cation recognition via cation metathesis within an ion pair receptor

Sung Kuk Kim, Gabriela I. Vargas-Zúñiga, Benjamin P. Hay, Neil J. Young, Lætitia H. Delmau, Charles Masselin, Chang Hee Lee, Jong Seung Kim, Vincent M. Lynch, Bruce A. Moyer, Jonathan L. Sessler

Research output: Contribution to journalArticlepeer-review

86 Citations (Scopus)


Ion pair receptor 3 bearing an anion binding site and multiple cation binding sites has been synthesized and shown to function in a novel binding-release cycle that does not necessarily require displacement to effect release. The receptor forms stable complexes with the test cesium salts, CsCl and CsNO 3, in solution (10% methanol-d 4 in chloroform-d) as inferred from 1H NMR spectroscopic analyses. The addition of KClO 4 to these cesium salt complexes leads to a novel type of cation metathesis in which the "exchanged" cations occupy different binding sites. Specifically, K + becomes bound at the expense of the Cs + cation initially present in the complex. Under liquid-liquid conditions, receptor 3 is able to extract CsNO 3 and CsCl from an aqueous D 2O layer into nitrobenzene-d 5 as inferred from 1H NMR spectroscopic analyses and radiotracer measurements. The Cs + cation of the CsNO 3 extracted into the nitrobenzene phase by receptor 3 may be released into the aqueous phase by contacting the loaded nitrobenzene phase with an aqueous KClO 4 solution. Additional exposure of the nitrobenzene layer to chloroform and water gives 3 in its uncomplexed, ion-free form. This allows receptor 3 to be recovered for subsequent use. Support for the underlying complexation chemistry came from single-crystal X-ray diffraction analyses and gas-phase energy-minimization studies.

Original languageEnglish
Pages (from-to)1782-1792
Number of pages11
JournalJournal of the American Chemical Society
Issue number3
Publication statusPublished - 2012 Jan 25

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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