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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (07): 805-809. 上一篇    下一篇

研究论文

几种取代胡椒醛缩合不对称卟啉化合物的合成及结构表征

赵胜芳*,1,2，陈年友1，程兴安1，朱其凤2，李早英2   

  1. (1黄冈师范学院化学系 黄冈 438000)
    (2武汉大学化学与分子科学学院 武汉 430072)
  • 收稿日期:2004-09-20 修回日期:2004-01-10 发布日期:2005-06-30
  • 通讯作者: 赵胜芳

Synthesis and Characterization of Novel Unsymmetrical Por-phyrins Condensed from Substituted Piperonal

ZHAO, Sheng-Fang*,1,2 CHEN, Nian-You1 CHENG, Xing-An1
ZHU, Qi-Feng2 LI, Zao-Ying2   

  1. (1 Department of Chemistry, Huanggang Normal University, Huanggang 438000)
    (2 College of Chemical and Molecular Sciences, Wuhan University, Wuhan 430072)
  • Received:2004-09-20 Revised:2004-01-10 Published:2005-06-30
  • Contact: ZHAO, Sheng-Fang

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1717

被引次数

23

利用微波加热法, 以6-硝基胡椒醛、两种R取代苯甲醛(R＝H, Cl)、吡咯为原料, 在丙酸中缩合, 合成了两种新的不对称卟啉化合物5-(2-硝基-4,5-亚甲二氧基)苯基-10,15,20-三苯基卟啉(2)和5-(2-硝基-4,5-亚甲二氧基)苯基-10,15, 20-三对氯苯基卟啉(3). 将2和3还原得到了化合物5-(2-氨基-4,5-亚甲二氧基)苯基-10,15,20-三苯基卟啉(4)和5-(2-氨 基-4,5-亚甲二氧基)苯基-10,15,20-三对氯苯基卟啉(5). 新化合物结构分别经UV-Vis, IR, 1H NMR及元素分析所证实. 荧光测试表明, 几个化合物都有比较好的荧光强度, 且氨基取代化合物的荧光强度比相应的硝基化合物的大.

关键词: 结构表征, 胡椒醛, 还原, 硝化, 微波合成, 不对称卟啉

Two unsymmetrical porphyrins of 5-(2-nitro-4,5-methylenedioxy)phenyl-10,15,20-triphenyl- porphyrin (2) and 5-(2-nitro-4,5-methylenedioxy)phenyl-10,15,20-tri(p-chlorophenyl)-porphyrin (3) were prepared using microwave irradiation. The reduction of 2 and 3 gave 5-(2-amino-4,5-methylenedioxy)- phenyl-10,15,20-triphenylporphyrin (4) and 5-(2-amino-4,5-methylenedioxy)phenyl-10,15,20-tri(p-chloro- phenyl)porphyrin (5). These novel porphyrins have been confirmed by UV-Vis, IR, 1H NMR spectra and elemental analysis.

Key words: nitration, structural characterization, unsymmetrical porphyrin, reduction, microwave synthesis, piperonal