Click synthesis of triazole-linked calix[4]arene ionophores. Potentiometric and ESI-MS screening of ion-selectivity

János B. Czirok, Gyula Jágerszki, Klára Tóth, Ágnes Révész, László Drahos, István Bitter

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A series of 1,2,3-triazole-linked calix[4]arene ionophores comprised of different O-donor groups (OH, COOEt, CONEt2) attached either to the lower rim of calix or to the triazole moieties were synthesized to explore their ion-selectivity for the first time in potentiometric transduction. Plasticized PVC membrane electrodes (ISEs) were fabricated, and their potentiometric selectivities were measured toward a series of mono- and divalent metal ions. Structure-ion-selectivity relationship and the structural requirements of the coordination sphere for selective binding were established. ISEs made of calix[4]arene-bis-triazoles were found generally to exhibit distinct Ag + selectivity in the order 3 ≈ 4 > 2 > 1, indicating the beneficial effect of the carboxamide or ester groups in the complexing site. In contrast, calix[4]arene-tetratriazole 5 comprised only sp 2 N-donor atoms displayed excellent Cu2+ selectivity over a series of alkali-, alkaline earth- and transition metal ions. A unique feature of the outstanding Ag+ selective electrodes made of 3 and 4 was recognized and suggested their potential application as Na+ ISEs in systems not containing silver ions. Further, the potential use of competitive ESI-MS experiments for screening the binding affinities of ionophores 3-6 to different metal ions was also demonstrated.

Original languageEnglish
Pages (from-to)207-215
Number of pages9
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume78
Issue number1-4
DOIs
Publication statusPublished - Apr 2014

Keywords

  • 1,2,3-Triazole
  • Calix[4]arene ionophore
  • Click chemistry
  • ESI-MS
  • Ion-selectivity
  • PVC membrane electrode

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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