Syntheses of Diaza-18-Crown-6 Ligands Containing Two Units Each of 4-Hydroxyazobenzene, Benzimidazole, Uracil, Anthraquinone, or Ferrocene Groups

Abstract

Six diaza-18-crown-6 ligands each containing two aromatic side arms with responsive functions were prepared. Diaza-18-crown-6 containing two 4-hydroxyazobenzene or two 4- hydroxy-4'-(dimethylamino)-azobenzene (3 or 4) substituents were prepared via a one-pot Mannich reaction. Diaza-1 8-crown-6 containing two berizimidazole (5), two uracil (6) or two 9,10-anthraquinone (7) substituents were prepared by treating the diazacrown with the appropriate chloromethyl-containing compound. Reductive amination using sodium triacetoxyborohydride, diaza-18-crown-6 and ferrocenecarboxaldehyde was used to prepare bisferrocene-substituted diaza-18-crown-6 (3). Interactions of compounds 3, 5, and 6 with Na(+), K(+), Ba(2+), Ag(+), and Cu(2+) were evaluated by a calorimetric titration technique at 25 deg C in methanol. All three ligands form more stable complexes with Ag(+) and Cu(2+) (5 forms a precipitate with Ag(+)) than with Na(+) and K(+). Ligand 5 also forms a highly stable complex with Ba(2+).

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Document Details

Document Type
Technical Report
Publication Date
Apr 06, 1999
Accession Number
ADA361715

Entities

People

  • Jerald S. Bradshaw
  • Krzystof E. Krakowiak
  • Ning Su
  • Paul B. Savage
  • Xian X. Zhang

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  • Brigham Young University

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  • Biochemistry
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  • Chemistry

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