Cesium Halide Ion Pair Recognition by a Pyrrole Strapped Calix[4]pyrrole

Supramolecular Chemistry
Ju Ho YangSung Kuk Kim

Abstract

The binding properties of the pyrrole-strapped calix[4]pyrrole 2 for cesium halide ion pairs were studied via1H NMR spectroscopic and single crystal X-ray diffraction analyses. Receptor 2 was found to bind CsF, CsCl, and CsBr in the solid state and in chloroform/methanol (4/1, v/v) solution with relatively high affinity as compared with the parent calix[4]pyrrole 1. It was also revealed by solid-liquid extraction experiments that receptor 2 was capable of solubilizing CsF in CDCl3, a medium in which this salt is otherwise insoluble. Single crystal X-ray diffraction analyses and 1H NMR spectroscopic data recorded in 20% CD3OD in CDCl3 provide support for the suggestion that the strap pyrrolic NH proton of 2, as well as those of the calix[4]pyrrole framework, contribute to anion recognition, thus increasing affinity for cesium halide salts relative to the parent system 1. In the solid state, receptor 2 interacts with CsF to form a two dimensional coordination polymer in the presence of methanol. A linear coordination polymer is observed in the case of CsCl and CsBr. Receptor 2 was also found to form a complex with CsF in chloroform/methanol (4/1, v/v) solution, albeit with a different binding mode than is seen in the solid state.

References

Apr 23, 2005·Angewandte Chemie·Radu CustelceanPhilip A Gale
Mar 4, 2008·Journal of the American Chemical Society·Matthieu P WintergerstLaetitia H Delmau
Apr 11, 2008·Chemical Communications : Chem Comm·Chang-Hee LeeJonathan L Sessler
Dec 3, 2008·Chemical Communications : Chem Comm·Christine C TongPhilip A Gale
Aug 26, 2010·Chemical Society Reviews·Sung Kuk Kim, Jonathan L Sessler
Dec 15, 2010·The Journal of Organic Chemistry·Sung Kuk KimJonathan L Sessler
Jan 7, 2011·Accounts of Chemical Research·Philip A Gale
Jan 11, 2011·Journal of Inclusion Phenomena and Macrocyclic Chemistry·Dustin E GrossJonathan L Sessler
Mar 16, 2012·Angewandte Chemie·Anna J McConnell, Paul D Beer
Jul 1, 2014·Accounts of Chemical Research·Sung Kuk Kim, Jonathan L Sessler
Jan 23, 2015·Journal of the American Chemical Society·Moira CiardiPablo Ballester
Jul 22, 2016·Journal of the American Chemical Society·Qing HeJonathan L Sessler
Feb 15, 2018·The Journal of Organic Chemistry·Seung Hyeon KimSung Kuk Kim

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Citations

Jan 21, 2020·Chemical Society Reviews·Sangshan PengJonathan L Sessler
Nov 10, 2020·Journal of the American Chemical Society·Francesco IbbaVéronique Gouverneur

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Methods Mentioned

BETA
X-ray
NMR

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