Ferrocene-amino acid macrocycles as hydrazone-based receptors for anions

Sophie R. Beeren, Jeremy K M Sanders

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

We report the synthesis of a family of new macrocyclic hydrazone-based anion receptors. Formed from the reaction between isophthalaldehyde and a helical amino acid-disubstituted ferrocene dihydrazide, these macrocycles contain from one to eight ferrocene moieties. The isolation of the four smallest of the macrocycles and their characterisation by UV-Vis, CD and NMR spectroscopy is described. The conformation of the macrocycles is explored, particularly with reference to the formation of a helical intramolecularly hydrogen-bonded structure. An investigation of the use of these macrocycles as anion-receptors shows that they are all effective hosts; the larger macrocycles show the highest affinities for anions. Studies using NMR spectroscopy suggest that the anion-recognition results primarily from the formation of multiple hydrogen bonds between the anions and the electropositive N-H protons of the acylhydrazones.
Original languageEnglish
JournalChemical Science
Volume2
Issue number8
Pages (from-to)1560-1567
Number of pages8
ISSN2041-6520
DOIs
Publication statusPublished - 2011
Externally publishedYes

Keywords

  • Chemistry (all)
  • Anion receptor
  • Ferrocene moiety
  • Ferrocenes
  • Hydrogen-bonded structures
  • Macrocycles
  • Macrocyclics
  • Amino acids
  • Hydrogen bonds
  • Iron compounds
  • Nuclear magnetic resonance spectroscopy
  • Organometallics
  • Synthesis (chemical)
  • Negative ions

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