冠醚桥接苯并菲二聚体合成的新途径.pdfVIP

2010 年第 30 卷 有 机 化 学 Vol. 30, 2010 第 4 期, 590～594 Chinese Journal of Organic Chemistry No. 4, 590～594 ·研究论文· 冠醚桥接苯并菲二聚体合成的新途径 李娟娟 何志群* 许 敏 孔翔飞 张春秀 (北京交通大学理学院光电子技术研究所 教育部发光与光信息技术重点实验 北京 100044) 摘要 本研究借鉴合成冠醚的 Willianmson 反应, 通过缓慢滴加二氯乙醚合成了重要中间体乙氧基醚链接的苯并菲二 聚体, 且避免了 2,3-二羟基四戊烷氧基苯并菲自身成环反应所导致单一冠醚苯并菲的生成. 进一步以该中间体为原料, 通过缩合反应, 最终得到了冠醚桥接苯并菲二聚体, 并用 1H NMR, 13C NMR 和 MALDI-TOF 质谱对产物的结构和纯度 进行了表征. 关键词 Willianmson; 苯并菲; 二聚体; 冠醚 A Synthetic Route towards a Crown-Ether Linked Triphenylene Dimer Li, Juanjuan He, Zhiqun* Xu, Min Kong, Xiangfei Zhang, Chunxiu (Key Laboratory of Luminescence and Optical Information, Ministry of Education, Institute of Optoelectronic Technology, Beijing Jiaotong University, Beijing 100044) Abstract According to Willianmson reaction for the synthesis of crown ether ring, a very important inter- mediate, alkoxy-chain linked two triphenylene moieties was synthesized successfully through a slow addi- tion of bis(2-chloroethyl) ether to avoid the production of crown ether ring on single triphenylene from 2,3-dihydroxy-tetrakis(pentyloxy)-triphenylene. Furthermore, a crown ether bridged triphenylene dimer was finally achieved via the condensation reaction of bis(2-chloroethyl) ether with the intermediate. The final 1 13 product was characterized by H NMR, C NMR and MALDI-TOF spectra. Keywords Willianmson; triphenylene; dimer; crown ether 有机半导体材料, 特别是具有大 π 健共轭分子结构 轭刚性中心核铺开而形成伸展的碳氢结构. 若提高其饱 的盘状分子材料, 由于可以