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).

Keywords

ChemistryIntramolecular forceImineAmine gas treatingRedoxCharge (physics)Intramolecular reactionPhotochemistryStereochemistryOrganic chemistryCatalysis

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Year
2011
Type
article
Volume
76
Issue
22
Pages
9504-9506
Citations
7
Access
Closed

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Cite This

Tomohito Ide, Daisuke Takeuchi, Kohtaro Osakada et al. (2011). Aromatic Macrocycle Containing Amine and Imine Groups: Intramolecular Charge-Transfer and Multiple Redox Behavior. The Journal of Organic Chemistry , 76 (22) , 9504-9506. https://doi.org/10.1021/jo201650t

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DOI
10.1021/jo201650t