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Aromatic Macrocycle Containing Amine and Imine Groups: Intramolecular Charge-Transfer and Multiple Redox Behavior

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posted on 2016-02-22, 14:31 authored by Tomohito Ide, Daisuke Takeuchi, Kohtaro Osakada, Takashi Sato, Masayoshi Higuchi
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 (E1/2 = 0.03 V vs Ag/Ag+) and of oxidation of amino groups of higher potentials (0.60 and 0.77 V).