A Calix[4]arene Strapped Calix[4]pyrrole: An Ion-Pair Receptor Displaying Three Different Cesium Cation Recognition Modes
DC Field | Value | Language |
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dc.contributor.author | Kim, Sung Kuk | - |
dc.contributor.author | Sessler, Jonathan L. | - |
dc.contributor.author | Gross, Dustin E. | - |
dc.contributor.author | Lee, Chang-Hee | - |
dc.contributor.author | Kim, Jong Seung | - |
dc.contributor.author | Lynch, Vincent M. | - |
dc.contributor.author | Delmau, Laatitia H. | - |
dc.contributor.author | Hay, Benjamin P. | - |
dc.date.accessioned | 2021-09-08T03:46:50Z | - |
dc.date.available | 2021-09-08T03:46:50Z | - |
dc.date.created | 2021-06-11 | - |
dc.date.issued | 2010-04-28 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/116616 | - |
dc.description.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% CD3OD in CDCl3 (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 center dot CsF cation recognition takes place within the receptor cavity itself, as inferred from both single-crystal X-ray diffraction analyses and H-1 NMR spectroscopic studies. This binding mode is supported by calculations carried out using the MMFF94 force field model. In 10% CD3OD in CDCl3 (v/v), receptor 2 shows selectivity for CsF over the Cs+ salts of Cl-, Br-, and NO3- 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 H-1 NMR spectroscopic studies reveal that receptor 2 forms a 1:1 complex with CsNO3, 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. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | ANION-BINDING AGENTS | - |
dc.subject | 1,3-ALTERNATE CONFORMATION | - |
dc.subject | MACROBICYCLIC RECEPTOR | - |
dc.subject | MOLECULAR RECOGNITION | - |
dc.subject | LIQUID-EXTRACTION | - |
dc.subject | CROWN-ETHERS | - |
dc.subject | LOGIC GATES | - |
dc.subject | COMPLEXATION | - |
dc.subject | METAL | - |
dc.subject | HIGHLIGHTS | - |
dc.title | A Calix[4]arene Strapped Calix[4]pyrrole: An Ion-Pair Receptor Displaying Three Different Cesium Cation Recognition Modes | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Kim, Jong Seung | - |
dc.identifier.doi | 10.1021/ja100715e | - |
dc.identifier.scopusid | 2-s2.0-77952566807 | - |
dc.identifier.wosid | 000276991700067 | - |
dc.identifier.bibliographicCitation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.132, no.16, pp.5827 - 5836 | - |
dc.relation.isPartOf | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.citation.title | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.citation.volume | 132 | - |
dc.citation.number | 16 | - |
dc.citation.startPage | 5827 | - |
dc.citation.endPage | 5836 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.subject.keywordPlus | ANION-BINDING AGENTS | - |
dc.subject.keywordPlus | 1,3-ALTERNATE CONFORMATION | - |
dc.subject.keywordPlus | MACROBICYCLIC RECEPTOR | - |
dc.subject.keywordPlus | MOLECULAR RECOGNITION | - |
dc.subject.keywordPlus | LIQUID-EXTRACTION | - |
dc.subject.keywordPlus | CROWN-ETHERS | - |
dc.subject.keywordPlus | LOGIC GATES | - |
dc.subject.keywordPlus | COMPLEXATION | - |
dc.subject.keywordPlus | METAL | - |
dc.subject.keywordPlus | HIGHLIGHTS | - |
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