Selective nitrate recognition by a halogen-bonding four-station [3]rotaxane molecular shuttle

Andrew Docker, Igor Marques, Vítor Félix, Paul D. Beer*, Timothy Barendt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

59 Citations (Scopus)
127 Downloads (Pure)

Abstract

The synthesis of the first halogen bonding [3]rotaxane host system containing a bis-iodo triazolium-bis-naphthalene diimide four station axle component is reported. Proton NMR anion binding titration experiments revealed the halogen bonding rotaxane is selective for nitrate over the more basic acetate, hydrogen carbonate and dihydrogen phosphate oxoanions and chloride, and exhibits enhanced recognition of anions relative to a hydrogen bonding analogue. This elaborate interlocked anion receptor functions via a novel dynamic pincer mechanism where upon nitrate anion binding, both macrocycles shuttle from the naphthalene diimide stations at the periphery of the axle to the central halogen bonding iodo-triazolium station anion recognition sites to form a unique 1:1 stoichiometric nitrate anion–rotaxane sandwich complex. Molecular dynamics simulations carried out on the nitrate and chloride halogen bonding [3]rotaxane complexes corroborate the1H NMR anion binding results.

Original languageEnglish
Pages (from-to)11069-11076
Number of pages8
JournalAngewandte Chemie - International Edition
Volume55
Issue number37
DOIs
Publication statusPublished - 20 Jul 2016

Keywords

  • halogen bonding
  • molecular devices
  • molecular dynamics
  • rotaxanes
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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