New polydentate inacrocyclic ligands of hybrid amine-imine and amide-imine types as artificial anion receptors. Synthesis and study of anion binding

E. A. Katayev, G. D. Pantos, V. M. Lynch, J. L. Sessler, M. D. Reshetova, Y. A. Ustynyuk

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Three new macrocyclic Schiff bases containing an amine or amide structural fragment along with imine groups were synthesized by condensation of 2,6-bis(2-aminophenyliminomethyl)pyridine (1) and NN'-bis(2-aminophenyl)pyridine-2,6-dicarboxamide (2) with 2,5-diformylpyrrole (3) and 2,2 -bis(5-formylpyrrol-2-yl)propane (4). The reaction of compound I with 3 proceeds abnormally and is accompanied by redox disproportionation of compound 1 in the first step. The structure of the macrocyclic product of this reaction was established by X-ray diffraction analysis. Spectrophotometric titration showed that hybrid macrocycle 10, which was prepared by condensation of compound 2 with 4, possesses the properties of an anion receptor and selectively binds hydrosulfate and dihydrophosphate anions in the presence of bromide and nitrate anions. The structures of 10 and its adduct with the hydrosulfate anion were calculated by density functional theory.
Original languageEnglish
Pages (from-to)165-172
Number of pages8
JournalRUSSIAN CHEMICAL BULLETIN
Volume54
Issue number1
DOIs
Publication statusPublished - 1 Jan 2005

Keywords

  • macrocycles
  • Schiff bases
  • X-ray diffraction analysis
  • spectrophotometry
  • anion receptors
  • density functional theory

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