李娜 花文杰

摘 要：五氟苯和五氟溴苯是公认的代表性的含氟化合物，可以通过多种反应与其它化合物相连接。N-芳化杂环化合物例如咔唑和吲哚是具有空穴传输性能、在紫外光范围有很强的吸收并且具有发可贵的蓝光等特性。以咔唑为侧基的非共轭类聚合物具有很好的光学性能和空穴传输性能。呋喃噻吩齐聚物具有优异的性质。该文发展了合成咔唑-呋喃-噻吩以及吲哚-呋喃-噻吩齐聚物的方法。以自制的五氟苯代吲哚和五氟苯代咔唑为起始原料，与硼试剂反应分别制备相应的硼酸酯。通过溴封端的噻吩-氟代呋喃-噻吩中间体与硼酸酯反应制备咔唑-呋喃噻吩以及吲哚-呋喃-噻吩齐聚物。

关键词：咔唑 吲哚 噻吩 呋喃

中图分类号：O63 文献标识码：A 文章编号：1674-098X（2015）05（b）-0017-03

Synthesis of Carbazole-Furan-Thiophene and Indole Furan-Thiophene Oligomers

Li Na Hua Wenjie

（Shanghai Institute of Organic Chemistry， Chinese Academy of Sciences， Shanghai， 200032，China）

Abstract：Pentafluorophenyl and pentafluoroethyl bromobenzene is recognized as a class of fluorochemical representative， can be connected to other compounds by a variety of reactions.N-arylation heterocyclic compounds such as carbazole and indole is a hole transport properties in the UV range and has a strong absorption of valuable blue light and other features.Carbazole is a side group of non-conjugated polymer with good optical properties and hole transport properties. Furan thiophene oligomers have excellent properties. This paper developed a new method for the synthesis of carbazole-furan-thiophene and indole-furan-thiophene oligomer.Pentafluorophenyl substituting indole and carbazole as starting material， under the action of boron， the corresponding boronate ester were synthesized.Bromine-capped thiophene- fluoro-furan-thiophene intermediate was produced， and then it was reacted with boric acid esters，prepared carbazole-furan thiophene and indole-furan-thiophene oligomers.

Key Words：Indole；Zarbazole；Furan；Thiophene

單分散共轭齐聚物具有确定的分子结构，可以获得高纯度的材料，并且易于表征，结构与性能关系直接，是研究共轭聚合物分子结构与光电性能的理想模型[1]。噻吩类齐聚物OTFTs器件的场致迁移率（μFET）达到0.1-1.0cm2/V·s，与非晶硅器件接近[2]。以噻吩为共轭单元，可以设计合成具有不同结构的共轭聚合物和齐聚物，调控其性质。呋喃及多取代呋喃不仅是许多重要天然产物和药物的基本结构单元，也是有机合成中重要的中间体。将呋喃环引入到噻吩齐聚物中，能使不含烷烃链噻吩呋喃齐聚物溶解于常规溶剂，明显改善了噻吩齐聚物的溶解性，并且引起更低的接触电阻，有利于光电器件性能的提高[3]。……