title: Rational design of a macrocyclic-based chemosensor for anions.
abstract: A macrocyclic-based fluorescence chemosensor has been designed and synthesized from the reaction of dansyl chloride and a hexaaminomacrocycle containing four secondary and two tertiary amines. The new chemosensor has been examined for its binding ability toward phosphate, sulfate, nitrate, iodide, bromide, chloride, and fluoride by fluorescence spectroscopy in DMSO. The results indicate that the compound binds each of the anions with a 1:1 stoichiometry, showing high affinity for the oxoanions, chloride and iodide with the binding constants up to four orders of magnitude. Ab initio calculations based on density functional theory (DFT) suggest that the ligand is deformed in order to encapsulate an anion, and each anion, except fluoride, is bonded to the macrocycle through two NH…X(-) and four CH…X(-) interactions.
authors.affiliation: Department of Chemistry and Biochemistry, Jackson State University, 1400 J. R. Lynch Street, P.O. Box 17910, Jackson, MS 39212, USA.
authors.forename: Kalpana R
authors.initials: KR
authors.lastname: Dey
authors.forename: Bryan M
authors.initials: BM
authors.lastname: Wong
authors.forename: Md Alamgir
authors.initials: MA
authors.lastname: Hossain
references.citation: Tetrahedron Lett. 2009 Nov 25;50(47):6537-6539
references.pmid: 20526453
references.citation: CrystEngComm. 2010 Jan 1;12(3):674-676
references.pmid: 20228881
references.citation: Inorg Chem. 2001 Aug 27;40(18):4710-20
references.pmid: 11511220
references.citation: Acc Chem Res. 2006 Jul;39(7):465-75
references.pmid: 16846210
references.citation: J Am Chem Soc. 2005 Jun 15;127(23):8282-3
references.pmid: 15941251
references.citation: J Comput Chem. 2009 Jan 15;30(1):51-6
references.pmid: 18504779
references.citation: Inorg Chem. 2005 Oct 17;44(21):7540-6
references.pmid: 16212380
references.citation: Chem Soc Rev. 2009 Feb;38(2):520-63
references.pmid: 19169465
references.citation: J Fluoresc. 2005 May;15(3):267-85
references.pmid: 15986153
references.citation: ACS Appl Mater Interfaces. 2009 Nov;1(11):2529-35
references.pmid: 20356123
references.citation: Dalton Trans. 2006 Aug 14;(30):3678-84
references.pmid: 16865180
references.citation: J Am Chem Soc. 2010 Jan 13;132(1):147-56
references.pmid: 19958001
references.citation: Org Lett. 2002 Jul 25;4(15):2449-52
references.pmid: 12123348
references.citation: Acc Chem Res. 2005 Aug;38(8):671-8
references.pmid: 16104690
references.citation: Acta Crystallogr Sect E Struct Rep Online. 2009 Sep 9;65(10):o2405-6
references.pmid: 20165564
references.citation: J Org Chem. 2007 Mar 30;72(7):2289-96
references.pmid: 17323997
references.citation: Chem Rev. 2003 Nov;103(11):4419-76
references.pmid: 14611267