有机化学 ›› 2012, Vol. ›› Issue (03): 552-559.DOI: 10.6023/cjoc1107151 上一篇    下一篇

研究论文

芴2,7 位取代的9,9'-二芳基螺芴类化合物的合成及性能

欧阳密, 余振伟, 张玉建, 项文勤, 胡彬, 张诚   

  1. 浙江工业大学化学工程与材料学院 绿色化学合成技术国家重点实验室培育基地 科技部能源材料及应用国际合作基地 杭州 310014
  • 收稿日期:2011-07-15 修回日期:2011-10-25 出版日期:2012-03-25 发布日期:2012-03-24
  • 通讯作者: 张诚 E-mail:czhang@zjut.edu.cn
  • 基金资助:

    国家重点基础研究发展计划(No. 973 计划)(Nos. 2010CB635108, 2011CBA00700)与国际科技合作与交流(No. S2012ZR0152)资助项目.

Synthesis and Properties of 9,9'-Diarylspriofluorene with Substituted Group at 2,7-Position of Fluorene

Ouyang Mi, Yu Zhenwei, Zhang Yujian, Xiang Wenqin, Hu Bin, Zhang Cheng   

  1. International Science and Technology Cooperation Base of Energy Materials and Application, State Key Laboratory Breeding Base for Green Chemistry Synthesis Technology, College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014
  • Received:2011-07-15 Revised:2011-10-25 Online:2012-03-25 Published:2012-03-24
  • Supported by:

    Project supported by the National Basic Research Program of China (Nos. 2010CB635108, 2011CBA00700) and the International Technical Cooperation and Exchanges (No. S2012ZR0152)

设计并合成了一系列以三苯胺为核, 芴衍生物为外围基团的有机蓝光小分子, 该合成通过Suzuki 反应在9-芳基芴的2 位和(或)7 位引入相同或不同取代基作为模块, 并利用Friedel-Crafts 反应将4-甲基三苯胺与这一系列模块结合.用NMR, MS 和元素分析进行结构表征. 荧光测试结果表明该类化合物溶液的荧光发射波长范围在442~466 nm 之间,属蓝光发射. 电化学测试显示该类材料的HOMO能级位于-5.15~-5.19 eV 之间. 差示扫描量热仪与热重分析得出化合物的玻璃化转变温度在166 ℃以上, 热分解温度高于398 ℃, 表明该类材料具有良好的热稳定性.

关键词: 9,9’-二芳基螺芴, Suzuki 反应, Friedel-Crafts 反应, 热稳定性

A series of novel 2-/2,7-(di)arylfluorene building-blocks were synthesized and utilized to prepare novel organic blue-emitting oligomers via Suzuki reaction and Friedel-Crafts reaction. The desired oligomers contained the 4-methyltriphenylamine core and fluorene derivatives peripheries. Their structures were confirmed by NMR and MS techniques and elemental analysis. The maximum photoluminescence (PL) emission wavelengths of the compounds ranged from 442 to 466 nm. Cyclic voltammetry (CV) showed that the highest occupied molecular orbital (HOMO) energy level of the compounds was located between -5.15 and -5.19 eV. The results of differential scanning calorimeter (DSC) and thermogravimetric (TG) indicated that these materials had excellent thermal stability with glass transition temperature of higher than 166 ℃ and thermal-decomposition temperature over 398 ℃.

Key words: 9,9’-diarylspirofluorene, Suzuki reaction, Friedel-Crafts reaction, thermal stability