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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (03): 299-303. 上一篇    下一篇

研究论文

2,2'-联吡啶参与的分子梭合成与1H NMR研究

卢锐亮，周冰，许新华*，张青丽，李言杰，方敬坤   

  1. (湖南大学化学化工学院 长沙 410082)
  • 收稿日期:2003-10-14 修回日期:2004-09-22 发布日期:2005-02-28
  • 通讯作者: 许新华

Synthesis of Molecular Shuttle Containing the Unit of 2,2'-Bipyridine and Study of Its 1H NMR

LU Rui-Liang,ZHOU Bing,XU Xin-Hua*,ZHANG Qing-Li
LI Yan-Jie,FANG Jing-Kun   

  1. (College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
  • Received:2003-10-14 Revised:2004-09-22 Published:2005-02-28
  • Contact: XU Xin-Hua

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2-{2-[4-苯基-二(4-特丁基苯基)甲基]苯氧基}乙氧乙醇磺酸酯(1)与4,4'-联吡啶在乙腈中回流36 h, 随后通过阴离子交换得到N-{2-{2-[4-苯基-二(4-特丁基苯基)甲基]苯氧基}乙氧乙基}-4,4'-联吡啶六氟磷酸盐(3), 产率为93.4%. 3与4,4'-二(溴甲基)-2,2'-联吡啶在乙腈中、70 ℃下反应72 h, 生成哑铃型化合物5, 产率为45%. 5与冠醚BPP34C10在55 ℃下搅拌5 d, 得到分子梭6和7, 产率分别为42.3%和27.3%. 1H NMR数据表明, 富电子冠醚BPP34C10与哑铃型组分上贫电子4,4'-联吡啶的非键作用使4,4'-联吡啶上氢的化学位移向高场有较大移动.

关键词: 合成, 冠醚, 2,2'-联吡啶, 自组装, 分子梭

The reaction of the tosylate 1 of 2-{2-{4-[1-phenyl-1,1-bis(4-tert-butylphenyl)methyl]phenoxy}ethoxy}ethanol with 4,4-bipyridine in CH3CN under refluxing for 36 h afforded N-{2-{2-{4- [1-phenyl-1,1-bis(4-tert-butylphenyl)methyl]phenoxy}ethoxy}ethyl}-4,4-bipyridinium tosylate (2), and 2 exchanged anion with NH4PF6 to give hexafluoro-phosphate 3 in 93.4%. The compound reacted with 4,4'-di(bromo methyl)-2,2'-bipyridine to give the dumbbell-shaped compound 5 in 45% yield. The molecular shut-tles 6 and 7 were synthesized by the self assembly of the dumbbell-shaped compound 5 and bisparaphenylene-34-crown-10. The 1H NMR data indicated that noncovalent interaction between the bipyridinium and crown ether provoked a considerable high-field shift.

Key words: synthesis, #NAME?, crown ether, self assembly, molecular shuttle, 2,2