Journal of the American Chemical Society, volume 132, issue 16, pages 5827-5836
A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes.
Kim Sung Kuk
1
,
Sessler Jonathan
1
,
Gross Dustin E.
1
,
Lee Chang Hee
1
,
Kim Jong S.
1
,
LYNCH VINCENT
1
,
Delmau L. H.
1
,
Hay Benjamin P
1
1
Department of Chemistry and Biochemistry, 1 University Station-A5300, The University of Texas at Austin, Austin, Texas 78712-0165, Department of Chemistry, Kangwon National University, Chun-Chon 200-701, Korea, Department of Chemistry, Korea University, Seoul 136-701, Korea, and Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, Tennessee 37830-6119
|
Publication type: Journal Article
Publication date: 2010-04-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
An ion-pair receptor, the calix[4]pyrrole-calix[4]arene pseudodimer 2, bearing a strong anion-recognition site but not a weak cation-recognition site, has been synthesized and characterized by standard spectroscopic means and via single-crystal X-ray diffraction analysis. In 10% CD(3)OD in CDCl(3) (v/v), this new receptor binds neither the Cs(+) cation nor the F(-) anion when exposed to these species in the presence of other counterions; however, it forms a stable 1:1 solvent-separated CsF complex when exposed to these two ions in concert with one another in this same solvent mixture. In contrast to what is seen in the case of a previously reported crown ether "strapped" calixarene-calixpyrrole ion-pair receptor 1 (J. Am. Chem. Soc. 2008, 130, 13162-13166), where Cs(+) cation recognition takes place within the crown, in 2.CsF cation recognition takes place within the receptor cavity itself, as inferred from both single-crystal X-ray diffraction analyses and (1)H NMR spectroscopic studies. This binding mode is supported by calculations carried out using the MMFF94 force field model. In 10% CD(3)OD in CDCl(3) (v/v), receptor 2 shows selectivity for CsF over the Cs(+) salts of Cl(-), Br(-), and NO(3)(-) but will bind these other cesium salts in the absence of fluoride, both in solution and in the solid state. In the case of CsCl, an unprecedented 2:2 complex is observed in the solid state that is characterized by two different ion-pair binding modes. One of these consists of a contact ion pair with the cesium cation and chloride anion both being bound within the central binding pocket and in direct contact with one another. The other mode involves a chloride anion bound to the pyrrole NH protons of a calixpyrrole subunit and a cesium cation sandwiched between two cone shaped calix[4]pyrroles originating from separate receptor units. In contrast to what is seen for CsF and CsCl, single-crystal X-ray structural analyses and (1)H NMR spectroscopic studies reveal that receptor 2 forms a 1:1 complex with CsNO(3), with the ions bound in the form of a contact ion pair. Thus, depending on the counteranion, receptor 2 is able to stabilize three different ion-pair binding modes with Cs(+), namely solvent-bridged, contact, and host-separated.
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Kim S. K. et al. A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes. // Journal of the American Chemical Society. 2010. Vol. 132. No. 16. pp. 5827-5836.
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Kim S. K., Sessler J., Gross D. E., Lee C. H., Kim J. S., LYNCH V., Delmau L. H., Hay B. P. A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes. // Journal of the American Chemical Society. 2010. Vol. 132. No. 16. pp. 5827-5836.
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TY - JOUR
DO - 10.1021/ja100715e
UR - https://doi.org/10.1021%2Fja100715e
TI - A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes.
T2 - Journal of the American Chemical Society
AU - Kim, Sung Kuk
AU - Hay, Benjamin P
AU - Sessler, Jonathan
AU - Gross, Dustin E.
AU - Lee, Chang Hee
AU - Kim, Jong S.
AU - LYNCH, VINCENT
AU - Delmau, L. H.
PY - 2010
DA - 2010/04/01 00:00:00
PB - American Chemical Society (ACS)
SP - 5827-5836
IS - 16
VL - 132
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2010_Kim,
author = {Sung Kuk Kim and Benjamin P Hay and Jonathan Sessler and Dustin E. Gross and Chang Hee Lee and Jong S. Kim and VINCENT LYNCH and L. H. Delmau},
title = {A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes.},
journal = {Journal of the American Chemical Society},
year = {2010},
volume = {132},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021%2Fja100715e},
number = {16},
pages = {5827--5836},
doi = {10.1021/ja100715e}
}
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Kim, Sung Kuk, et al. “A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes..” Journal of the American Chemical Society, vol. 132, no. 16, Apr. 2010, pp. 5827-5836. https://doi.org/10.1021%2Fja100715e.