Synthesis and X-ray crystallographic studies of novel proton-ionizable nitro- and halogen-substituted acridono-18-crown-6 chromo- and fluorogenic ionophores

Péter Huszthy, Borbála Vermes, Nikoletta Báthori, Mátyás Czugler

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Starting from acridono-18-crown-6 ligand 1 (Fig. 1) seven new proton-ionizable chromogenic and fluorogenic ionophores 2-8 (Fig. 1) containing NO2 group(s) and/or Br or Cl atom(s) in the aromatic rings were prepared by electrophilic substitution. The precursor macrocycle 1 was obtained by a modification of the reported procedure which made chromatography unnecessary in purification and gave higher yield. X-ray crystallographic studies of the complexes of acridono-18-crown-6 type ligands 1, 2, 3, 6 and 8 show that the proton-ionizable units are in the acridone tautomeric form and that the ligands invariably bind a water molecule in their cavities by multipodal hydrogen bonding. In two cases (6 and 8) an additional DMF solvent molecule is also bound at the crown perimeter in the solid state.

Original languageEnglish
Pages (from-to)9371-9377
Number of pages7
JournalTetrahedron
Volume59
Issue number47
DOIs
Publication statusPublished - Nov 17 2003

Keywords

  • Acridones
  • Chromogenic ionophores
  • Fluorogenic ionophores
  • Multipodal hydrogen bonding
  • Proton-ionizable crown ethers
  • X-ray crystallography

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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