高等学校化学学报

高等学校化学学报 ›› 2002, Vol. 23 ›› Issue (8): 1632.

• 研究论文 • 上一篇    下一篇

新型低聚噻吩衍生物的合成及其凝胶化性能研究

刘平1, 童真1, 邓文基2   

  1. 1. 华南理工大学材料研究所, 广州 510640;
    2. 华南理工大学应用物理系, 广州 510640
  • 收稿日期:2001-04-23 出版日期:2002-08-24 发布日期:2002-08-24
  • 通讯作者: hzslrc@public.guangzhou.gd.cn
  • 作者简介:刘平(1962年出生),男,博士,副教授,从事有机高分子材料研究.E-mail:hzslrc@public.guangzhou.gd.cn
  • 基金资助:

    教育部留学回国人员科学研究启动基金;科技部基础重大项目前期研究专项基金(批准号:2001-0350)资助

Synthesis and Gel-forming Properties of a Novel Class of Oligothiophene Derivatives

LIU Ping1, TONG Zhen1, DENG Wen-Ji2   

  1. 1. Research Institute of Materials Science, South China University of Technology, Guangzhou 510640, China;
    2. Department fo Applied Physics, South China University of Technology, Guangzhou 510640, Chian
  • Received:2001-04-23 Online:2002-08-24 Published:2002-08-24

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被引次数

34

摘要： 设计合成了一系列新型低聚噻吩衍生物N,N'-双十八烷基-5,5"-(2,2:5,2"-三噻吩)二酰胺[N,N'-distearyl-5,5"-(2,2:5,2"-terthiophene) dicarboxamide (DNC183T)]、N,N'-双烷烃基-5,5"-(3,3"-双辛烷基-2,2:5,2"-三噻吩)二酰胺[N,N'-dialkyl-5,5"-(3,3"-dioctyl-2,2:5,2"-terthiophene)dicarbox-amide(DNCnDOc3T,n=5,8,16,18)]及N,N'-双十八烷基-5,5-(3,3-双辛烷基-2,2:5,2":5",2-四噻吩)二酰胺[N,N'-distearyl-5,5-(3,3-dioctyl-2,2:5,2":5",2-tetrathiophene)-dicarboxamide(DNC18DOc4T)].研究结果表明,DNC183T和DNC5DOc3T同有机溶剂不形成凝胶.DNCnDOc3T(n=8,16,18)和DNC18DOc4T能同几种有机溶剂形成透明、半透明或不透明的凝胶.通过测定凝胶随温度变化的红外光谱(IR)、核磁共振氢谱(1HNMR)、紫外光谱(UV),揭示出形成有机低分子凝胶的驱动力不仅有分子间氢键,而且π-π相互作用也是一个非常重要的因素.偏光光学显微镜、扫描电子显微镜(SEM)显示出有机低分子凝胶呈三维网络结构.另外,DNC18Doc3T/盐/氰基苯凝胶体系在电场作用下发生可逆的颜色.

关键词: 有机低分子凝胶, 三噻吩, 四噻吩, 分子间氢键, 三维网络, 电致变色

Abstract: In order to develop a novel class of low molecular weight organic gels and to gain an insight into the relationship between molecular structure of gel forming compounds and gel forming properties, a novel family of low molecular weight organic compounds containing terthiophene and tetrathiophene, N, N'-dialkyl-5, 5" (2, 2":5, 2"-tetrathiophene)dicarboxamide(DNC183T), N, N'-dialkyl-5, 5" (3, 3" dioctyl 2, 2":5, 2"-tetrathiophene) dicarboxamide(DNCn DOc3T, n=5, 8, 16, 18) and N, N'-dialkyl-5, 5" (3, 3dioctyl 2, 2":5, 2":5", 2"-tetrathiophene) dicarboxamide(DNC18 DOc4T), were designed and synthesized. Whereas DNC18 3Tand DNC5DOc3Tdid not form gels with organic solvents, DNCn DOc3T (n=8, 16, 18) and DNC18 DOc4Twere found to form gels with certain organic solvents. These are the first examples of low molecular weight organic gels containing an oligothiophene moiety. It is of interest to note that while DNC8DOc3Tforms opaque gels with alcohols, such as ethanol and isopropanol, DNC16 DOc3T, DNC18 DOc3Tand DNC18 DOc4Tformed transparent gels with hydrocarbon solvents such as heptane, octane, undecane, and others. It is shown that the intermolecular hydrogen bonding and intermolecular interaction between the long alkyl chain in the Nalkylcarboxamide group as well as the incorporation of an alkyl group at the β position of the thiophene ring play an important role for the formation of gels. The xerogel showed three dimensional networks of fibrous bundle structure. DNC18 DOc3T/benzonitrile gel and DNC18 DOc4T/benzonitrile gel were found to function as a new type of electrochromic materials, exhibiting a reversible color changes on electrochemical oxidation and reduction.

Key words: Low molecular weight organic gel, Terthiophene, Tetrathiophene, Intermolecular hydrogen bonding, Three dimensional network, Electrochromism

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