4.6 Article

A Halogen-Bonding Bis-triazolium Rotaxane for Halide-Selective Anion Recognition

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 4, Pages 1660-1665

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405578

Keywords

anion binding; carbazoles; halogen bonding; host-guest systems; supramolecular chemistry

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A systematic study on the anion-binding properties of acyclic halogen-and hydrogen-bonding bis-triazolium carbazole receptors is described. The halide-binding potency of halogen-bonding bis-iodotriazolium carbazole receptors was found to be far superior to their hydrogen-bonding bis-triazolium-based analogues. This led to the synthesis of a mixed halogen-and hydrogen-bonding rotaxane host containing a bis-iodotriazolium carbazole axle component. The rotaxane's anion recognition properties, determined by H-1 NMR titration experiments in a competitive aqueous solvent mixture, demonstrated the preorganised halogen-bonding interlocked host cavity to be halide-selective, with a strong binding affinity for bromide.

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