Aromatic Macrocycle Containing Amine and Imine Groups. Intramolecular Charge-Transfer and Multiple Redox Behavior
Aromatic Macrocycle Containing Amine and Imine Groups. Intramolecular Charge-Transfer and Multiple Redox Behavior
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含有胺和亚胺基团的芳香大环。
DOI：
10.1021/jo201650t
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发表时间：
2011
期刊：
影响因子：
--
通讯作者：
Masayoshi Higuchi
中科院分区：
文献类型：
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作者：
Tomohito Ide;Daisuke Takeuchi;Kohtaro Osakada;Takashi Sato;Masayoshi Higuchi
蒽醌与二（4-氨基苯基）胺（苯胺二聚体）缩合得到一种二苯胺和醌二亚胺单元交替的环状化合物，产率为20%。所得的大环具有462 nm的吸收，这被分配到富电子的二苯胺单元和贫电子的蒽醌二亚胺单元之间的电荷转移跃迁。在酸性MeCN中的循环伏安法显示蒽醌二亚胺单元的氧化还原（E1/2= 0.03 V vs Ag/Ag+）和较高电位的氨基的氧化（0.60和0.77 V）。
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).