A doubly N-fused benzohexaphyrin and its rearrangement to a fluorescent macrocycle upon DDQ oxidation

被引:25
作者
Inokuma, Y
Matsunari, T
Ono, N
Uno, H
Osuka, A
机构
[1] Ehime Univ, Fac Sci, Dept Chem, Matsuyama, Ehime 7908577, Japan
[2] Ehime Univ, Integrated Ctr Sci, Matsuyama, Ehime 7908577, Japan
[3] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto, Japan
[4] Japan Sci & Technol Agcy, CREST, Sakyo Ku, Kyoto 6068502, Japan
关键词
fluorescence; macrocycles; oxidation; porphyrinoids; retro reactions;
D O I
10.1002/anie.200462815
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A retro-Diels-Alder reaction of a β-bicyclo[2.2.2]octadiene-fused precursor yields the doubly N-fused β-benzo[28]-hexaphyrin(1.1.1.1.1.1) shown, which undergoes oxidative rearrangement upon treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to yield a macrocycle that emits fluorescence in the visible/near-IR region. (Chemical Equation Presented) © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1856 / 1860
页数:5
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