Aromatic macrocycle containing amine and imine groups: intramolecular charge-transfer and multiple redox behavior.
J Org Chem
; 76(22): 9504-6, 2011 Nov 18.
Article
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| MEDLINE
| ID: mdl-21988558
ABSTRACT
A cyclic compound that has alternating diphenylamine and quinodiimine units was obtained by condensation of anthraquinone with bis(4-aminophenyl)amine (aniline dimer) in 20% yield. The resulting macrocycle has an absorption of 462 nm, which is assigned to charge transfer transitions between electron-rich diphenylamine units and electron-poor anthraquinone diimine units. Cyclic voltammetry in acidic MeCN shows redox of anthraquinone diimine units (E(1/2) = 0.03 V vs Ag/Ag(+)) and of oxidation of amino groups of higher potentials (0.60 and 0.77 V).
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Banco de datos:
MEDLINE
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En
Revista:
J Org Chem
Año:
2011
Tipo del documento:
Article
País de afiliación:
Japón