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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (10): 1215-1220. 上一篇    下一篇

研究论文

瓜环与4,4'-二氨基二苯甲烷衍生物的相互作用

杨守林†,1，薛赛凤1，马培华1，祝黔江1，陶朱*,1，张建新2   

  1. (1贵州大学应用化学研究所 贵阳 550025)
    (2贵州省天然产物重点化学实验室 贵阳 550002)
  • 收稿日期:2004-12-08 修回日期:2004-04-13 发布日期:2005-10-08
  • 通讯作者: 陶朱

Interaction of Cucurbit[n]urils with Bis{4-[(2,3 or 4-pyridyl)-methylamino]-phenyl}methane Derivatives

YANG Shou-Lin†,1,XUE Sai-Feng1,MA Pei-Hua1
ZHU Qian-Jiang1,TAO Zhu*,1,ZHANG Jian-Xin2   

  1. (1 Institute of Applied Chemistry, Guizhou University, Guiyang 550025)
    (2 Key Laboratory of Chemistry for Natural Products of Guizhou Province, Guiyang 550002)
  • Received:2004-12-08 Revised:2004-04-13 Published:2005-10-08
  • Contact: TAO Zhu

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1569

被引次数

11

合成了三种长链多芳环多胺基客体, 它们分别由三种醛基吡啶异构体与4,4'-二氨基二苯甲烷形成的Schiff碱还原而成, 并得到1H NMR以及质谱分析方法表征证实. 以核磁共振技术、紫外吸收光谱分析方法以及滴定1H NMR方法为研究手段, 对瓜环(cucurbit[n]urils, n＝6～8)分别与三种4,4'-二[N-(吡啶甲基)氨基]二苯甲烷盐酸盐相互作用进行了考察. 实验结果表明, 六元瓜环与三种4,4'-二[N-(吡啶甲基)氨基]二苯甲烷盐酸盐相互作用均形成物质的量之比为2∶1的哑铃型包结配合物; 八元瓜环与三种N,N'-二(N-(吡啶甲基)二苯甲烷盐酸盐相互作用形成以类轮烷结构为主的包结配合物; 七元瓜环与三种N,N'-二(N-(吡啶甲基)二苯甲烷盐酸盐相互作用存在多种模式的竞争.

关键词: 瓜环, 紫外吸收光谱分析, 客体, 包结配合物, 核磁共振技术

Three linear polyaromatic and polyamine guests were synthesized by reducing Schiff bases of three pyridinecarboxaldehyde isomers and bis(4-aminophenyl)methane, and characterized by 1H NMR and MS spectra. Investigation of the interaction and structures of cucurbit[n]urils (n＝6～8) with the title guests by using 1H NMR techniques and UV spectrum reveals that dumbbell shape inclusion complexes of cucurbit[6]uril with bis{4-[(2,3 or 4-pyridyl)methyl-amino]-phenyl}methane were formed with a molar ratio of 2∶1, and symmetrical pseu-dorotaxanes of cucurbit[8]uril-bis{4-[(2,3 or 4-pyridyl)methylamino]-phenyl}- methane were formed with a molar ratio of 1∶1. However, competitive models occur with interaction between cucurbit[7]uril with the guests respectively.

Key words: 1H NMR technique, guest, UV, inclusion complex, cucurbit[n]urils