高等学校化学学报

高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (11): 1945.

• 论文 • 上一篇    下一篇

双(对-氨基苯基)-2,3,7,8,12,13,17,18-八甲基卟啉及其金属衍生物的合成与表征

朱宝库, 魏秀珍, 徐又一, 徐志康   

  1. 浙江大学高分子科学研究所, 杭州 310027
  • 收稿日期:2002-08-20 出版日期:2003-11-24 发布日期:2003-11-24
  • 通讯作者: 朱宝库(1967年出生),男,博士,讲师,主要从事高分子功能膜研究.E-mail:zhubk@zju.edu.cn E-mail:zhubk@zju.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:50103010)资助

Synthesis and Characterization of meso-5,15-Bis(p-aminophenyl)-2,3,7,8,12,13,17,18-octamethyl-porphyrin and Its Metal Derivatives

ZHU Bao-KU, WEI Xiu-Zhen, XU You-Yi, XU Zhi-Kang   

  1. Institute of Polymer Science, Zhejiang University, Hangzhou 310027, China
  • Received:2002-08-20 Online:2003-11-24 Published:2003-11-24

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被引次数

3

摘要： 从3-甲基-2,4-戊二酮出发,经多步反应合成了3,3′,4,4′-四-甲基-2,2′-二吡咯基甲烷(TMDPM),改进了合成TMDPM的脱羧反应.研究了TMDPM与对-硝基苯甲醛反应合成meso-5,15-双-苯基-卟啉反应,发现对-甲基苯磺酸是卟啉原合成的良好催化剂,2,3-二-氯-5,6二氰基-1,4-苯醌是将卟啉原转化为卟啉的良好氧化剂;硝基卟啉经SnCl2还原成氨基卟啉后,用固-液抽提进行氨基卟啉的纯化,得到了5,15-双(对-硝基苯基)-2,3,7,8,12,13,17,18-八甲基卟啉、5,15-双(对-氨基苯基)-2,3,7,8,12,13,17,18-八甲基卟啉及其金属衍生物,并表征了其结构

关键词: 二吡咯基甲烷, 5, 15-双(对-硝基苯基)卟啉, 5, 15-双(对-氨基苯基)卟啉, 金属卟啉

Abstract: An important compound of 3,3′,4,4′-tetramethyl-2,2′-dipyrrolylmethane (TMDPM, 6) was synthesized through multi-step-reaction starting from 3-methyl-2,4-dipentadione.Therein, the reaction for converting 3,3′,4,4′-tetramethyl-2,2′-dipyrrolylmethane-5,5′-dicarbonate(5) to TMDPM waSImproved by substituting hydrazine witHEthanolamine as decarboxylation agent.The synthesis of meso-15,15-bis-phenyl-porphyrin by dipyrrolylmethane procedure waSInvestigated.It was found that p-toluenesulfonic acid was the efficient catalyst for condensation of compound 6 with nitrobenzaldehyde to porphyrinogen (7), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) was effective reagent for oxidizing of compound 7 to nitroporphyrin.After the hydrogenation of nitro-groups by SnCl2/concentrated HCl system to amino-groups, the extraction of the resulted aminoporphyrin by solid-mixture/chloroform process conducted better effects than aqueous-mixture/chloroform process.Following the methods aforesaid, several new porphyrin compoundSIncluding 5,15-bis(4-nitrophenyl)-2,3,7,8,12,13,17,18-octamethyl-porphyrin(BNPP, 8),5,15-bis(4-aminophenyl)-2,3,7,8,12,13,17,18-octamethyl-porphyrin(BAPP, 9) and metal-BAPP were synthesized.Their structures and absorption properties were characterized as well.

Key words: Dipyrrolylmethane, 5,15-Bis-(p-nitrophenyl)porphyrin, 5,15-Bis(p-aminophenyl)porphyrin, Metallic porphyrin

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