Calix[4]arene Schiff bases-potential ligands for fluorescent studies

M F Mahon, J McGinley, A D Rooney, J M D Walsh

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A series of novel double-armed calix[4]arene derivatives incorporating imine substituents were synthesised from the Schiff-base reaction of 2 5,2 7-bis[2-[(1-formyl-2-phenyl)oxy]ethyl-p-tert-butylcalix[4]arene (1) with the appropriate amine or hydrazone. All compounds were characterised by various spectroscopic and analytical techniques, and in three cases, by X-ray crystallographic studies. In the case of compound 2, inclusion compounds were synthesised with both m-xylene and dimethylformamide and their X-ray structures revealed these inclusion sites-between the pendant arms and in the upper cavity, respectively. In all cases, the pendant arms are bent away from each rather than adopting a face-to-face conformation.
Original languageEnglish
Pages (from-to)11058-11066
Number of pages9
JournalTetrahedron
Volume64
Issue number49
DOIs
Publication statusPublished - 2008

Keywords

  • NMR spectroscopy
  • Calix[4]arene
  • Inclusion
  • X-ray structure
  • Synthesis
  • Schiff bases

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