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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (10): 1282-1284. 上一篇    下一篇

研究简报

1,2-双[2-甲基-5-(3,4-二氟苯基)噻吩-3-基]全氟环戊烯的合成

刘太奇*，杨莉燕，于建香   

  1. (北京石油化工学院环境材料研究中心 北京 102617)
  • 收稿日期:2006-06-09 修回日期:2007-01-23 发布日期:2007-09-28
  • 通讯作者: 刘太奇

Synthesis of 1,2-Bis[2-methyl-5-(3,4-difluorophenyl)-3-thienyl]- perfluorocyclopentene

LIU Tai-Qi*,YANG Li-Yan,YU Jian-Xiang   

  1. (Research Center of Ecomaterial, Beijing Institute of Petro-chemical Technology, Beijing 102617)
  • Received:2006-06-09 Revised:2007-01-23 Published:2007-09-28
  • Contact: 刘太奇

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被引次数

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在冰浴条件下, 2-甲基噻吩(1)与液溴反应生成3,5-二溴-2-甲基噻吩(2); 在－78 ℃条件下, 硼酸三丁酯加入2, 得到2-甲基-3-溴-5-硼酸基噻吩(3); 3,4-二氟溴苯与3反应得到2-甲基-3-溴-5-(3,4-二氟苯基)噻吩(4); 在－78 ℃下全氟环戊烯与4反应, 得到一种新的二芳基乙烯类光致变色化合物1,2-双[2-甲基-5-(3,4-二氟苯基)噻吩-3-基]全氟环戊烯(DT-1). 用IR, NMR, MS和元素分析确定了化合物DT-1的结构, 并对该化合物的光致变色特性进行了初步研究.

关键词: 二芳基乙烯, 光致变色, 合成

2-Methylthiophene (1) was treated with liquid bromine to form 3,5-dibromo-2-methylthiophene (2) in ice bath, which reacted with tributyl borate to give 2-methyl-3-bromo-5-boronate thiophene (3) at －78 ℃. Treatment of 3 with 3,4-difluorobrombenzene gave 2-methyl-3-bromo-5-(3,4-difluorophenyl)- thiophene (4). Finally, a novel photochromic dithienylethene compound, 1,2-bis[2-methyl-5-(3,4-difluoro- phenyl)-3-thienyl]perfluorocyclopentene (DT-1), was synthesized by the reaction of 4 with perfluorocyclopentene at －78 ℃. The compound DT-1 was characterized by IR, NMR, MS spectra and elemental analysis, and its photochromic behavior was also discussed.

Key words: photochromism, synthesis, dithienylethene