Enantiomeric discrimination of chiral crown ether ionophores containing phenazine subcyclic unit by ion-selective potentiometry

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Abstract

In this paper the enatiomeric selectivity of two chiral phenazino-18-crown-6 ether hosts ((R, R)-1 and (R, R)-2) is quantified. These hosts were incorporated into plasticized PVC membranes and used as recognition elements of ion-selective electrodes. The potentiometric response towards the two enantiomers of 1-phenylethylammonium ions (PEA+) was measured. Potentiometric selectivity coefficients were calculated which reflect the ratio of the stability constants of the diastereomeric complexes. Ligand (R, R)-1 does not show enantiomeric recognition, while ligand (R, R)-2 has a slight preference for the (S)-(-) enantiomer over the (R)-(+) enantiomer manifested by a selectivity coefficient of 0.77. The results were compared to enantioselectivity patterns of the ligands towards α- (1-naphthyl)ethyl ammonium perchlorate (NEA+ClO-4) enantiomers measured by circular dichroism and by 1H NMR titrations.

Original languageEnglish
Pages (from-to)3-8
Number of pages6
JournalPeriodica Polytechnica Chemical Engineering
Volume54
Issue number1
DOIs
Publication statusPublished - Jan 1 2010

Keywords

  • Chiral crown ether
  • Enantiomeric selectivity
  • Ion-selective electrode
  • Ionophore
  • Phenazines

ASJC Scopus subject areas

  • Chemical Engineering(all)

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