Syntheses of Diaza-18-Crown-6 Ligands Containing Two Units Each of 4-Hydroxyazobenzene, Benzimidazole, Uracil, Anthraquinone, or Ferrocene Groups
BRIGHAM YOUNG UNIV PROVO UT DEPT OF CHEMISTRY AND BIOCHEMISTRY
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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, Ba2, Ag, and Cu2 were evaluated by a calorimetric titration technique at 25 deg C in methanol. All three ligands form more stable complexes with Ag and Cu2 5 forms a precipitate with Ag than with Na and K. Ligand 5 also forms a highly stable complex with Ba2.
- Inorganic Chemistry
- Organic Chemistry