Aromatic Macrocycle Containing
Amine and Imine Groups:
Intramolecular Charge-Transfer and Multiple Redox Behavior
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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 (<i>E</i><sub>1/2</sub> = 0.03 V vs Ag/Ag<sup>+</sup>) and of oxidation of amino groups of higher potentials (0.60
and 0.77 V)