title: Crown-6-calix[4]arene-capped calix[4]pyrrole: an ion-pair receptor for solvent-separated CsF ions.
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 (1)H 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.
authors.affiliation: Department of Chemistry and Biochemistry, 1 University Station-A5300, The University of Texas at Austin, Austin, Texas 78712-0165, USA. sessler@mail.utexas.edu
authors.forename: Jonathan L
authors.initials: JL
authors.lastname: Sessler
authors.forename: Sung Kuk
authors.initials: SK
authors.lastname: Kim
authors.forename: Dustin E
authors.initials: DE
authors.lastname: Gross
authors.forename: Chang-Hee
authors.initials: CH
authors.lastname: Lee
authors.forename: Jong Seung
authors.initials: JS
authors.lastname: Kim
authors.forename: Vincent M
authors.initials: VM
authors.lastname: Lynch
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D002586:Cesium / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry; D018360:Crystallography, X-Ray; D005459:Fluorides / Q000737:chemistry*; D007477:Ions; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry*
chemical_list: D043844:Crown Ethers; D007477:Ions; D010636:Phenols; D011166:Porphyrins; C121325:calix(4)arene; C520772:calix(4)arene-bis(crown-6-ether); C469811:calix(4)pyrrole; D047250:Calixarenes; D002586:Cesium; D005459:Fluorides; C027754:cesium fluoride
references.citation: Inorg Chem. 2004 Nov 29;43(24):7617-21
references.pmid: 15554626
references.citation: J Am Chem Soc. 2008 Mar 26;130(12):4129-39
references.pmid: 18311976
references.citation: J Org Chem. 2003 Aug 22;68(17):6720-5
references.pmid: 12919039
references.citation: Angew Chem Int Ed Engl. 2006 Jan 9;45(3):501-4
references.pmid: 16342124
references.citation: Chem Soc Rev. 2006 Dec;35(12):1269-86
references.pmid: 17225888
references.citation: Inorg Chem. 2004 Sep 20;43(19):5902-7
references.pmid: 15360239
references.citation: Angew Chem Int Ed Engl. 2005 Apr 22;44(17):2537-42
references.pmid: 15846831
references.citation: Chem Soc Rev. 2007 Feb;36(2):348-57
references.pmid: 17264935
references.citation: J Am Chem Soc. 2006 Sep 20;128(37):12281-8
references.pmid: 16967979
references.citation: J Org Chem. 2000 Apr 21;65(8):2386-92
references.pmid: 10789450
references.citation: J Am Chem Soc. 2001 Jun 20;123(24):5847-8
references.pmid: 11403637
references.citation: J Org Chem. 2004 Apr 16;69(8):2877-80
references.pmid: 15074945
references.citation: Chem Commun (Camb). 2008 Jan 7;(1):24-34
references.pmid: 18399401
references.citation: Angew Chem Int Ed Engl. 2001 Feb 2;40(3):486-516
references.pmid: 11180358
references.citation: Chem Rev. 2006 Nov;106(11):4585-621
references.pmid: 17091929
references.citation: J Org Chem. 2003 Dec 12;68(25):9819-20
references.pmid: 14656114
references.citation: Angew Chem Int Ed Engl. 2002 May 17;41(10):1757-9
references.pmid: 19750707
references.citation: J Am Chem Soc. 2005 Mar 9;127(9):2922-8
references.pmid: 15740128
references.citation: Chem Rev. 2004 May;104(5):2723-50
references.pmid: 15137805
references.citation: Chemistry. 2008;14(26):7822-7
references.pmid: 18645997