Syntheses of diaza-18-crown-6 ligands containing two units each of 4-hydroxyazobenzene, benzimidazole, uracil, anthraquinone, or ferrocene groups

Autor: Xian X. Zhang, Reed M. Izatt, Paul B. Savage, Krzysztof E. Krakowiak, Ning Su, Jerald S. Bradshaw
Rok vydání: 1999
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 36:771-775
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570360332
Popis: 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+).
Databáze: OpenAIRE
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