title: Halogen- and hydrogen-bonding catenanes for halide-anion recognition.
abstract: Halogen-bonding (XB) interactions were exploited in the solution-phase assembly of anion-templated pseudorotaxanes between an isophthalamide-containing macrocycle and bromo- or iodo-functionalised pyridinium threading components. (1)H NMR spectroscopic titration investigations demonstrated that such XB interpenetrated assemblies are more stable than analogous hydrogen bonding (HB) pseudorotaxanes. The stability of the anion-templated halogen-bonded pseudorotaxane architectures was exploited in the preparation of new halogen-bonding interlocked catenane species through a Grubbs' ring-closing metathesis (RCM) clipping methodology. The catenanes' anion recognition properties in the competitive CDCl(3)/CD(3) OD 1:1 solvent mixture revealed selectivity for the heavier halides iodide and bromide over chloride and acetate.
authors.affiliation: Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44) 1865-272690.
authors.forename: Lydia C
authors.initials: LC
authors.lastname: Gilday
authors.forename: Paul D
authors.initials: PD
authors.lastname: Beer
mesh_terms: D000838:Anions / Q000737:chemistry; D043863:Catenanes / Q000138:chemical synthesis / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D043862:Rotaxanes / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000838:Anions; D043863:Catenanes; D006219:Halogens; D043862:Rotaxanes
keywords: anions; catenanes; halogen bonding; molecular recognition; supramolecular chemistry