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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (10): 1208-1214. 上一篇    下一篇

研究论文

六～八元瓜环与咪唑[4,5-f]-1',10'-菲咯啉衍生物的相互作用

向双春1，陶朱*,2，胡育2，向章敏2
薛赛凤2，祝黔江2，张建新c   

  1. >(1贵州大学精细化工实验研究中心 贵阳 550025)
    (2贵州大学应用化学研究所 贵阳 550025)
    (3贵州省天然产物化学重点实验室 贵阳 550025)
  • 收稿日期:2004-11-08 修回日期:2005-04-13 发布日期:2005-10-08
  • 通讯作者: 陶朱

Interaction of Cucurbit[n]urils (n=6～8) with Imidazo[4,5-f]-1',10'-phenanthroline Derivatives

XIANG Shuang-Chun1, TAO Zhu*,2,HU Yu2,XIANG Zhang-Min2
XUE Sai-Feng2,ZHU Qian-Jiang2,ZHANG Jian-Xin3   

  1. (1 Center for Research and Development of Fine Chemical, Guizhou University, Guiyang 550025)
    ( 2 Institute of Applied Chemistry, Guizhou University, Guiyang 550025)
    (3 Key Laboratory of Chemistry for Natural Products of Guizhou Province, Guiyang 550002)
  • Received:2004-11-08 Revised:2005-04-13 Published:2005-10-08
  • Contact: TAO Zhu

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合成了2-苯基-咪唑[4,5-f]-1',10'-菲咯啉和对二甲氨基-2-苯基-咪唑[4,5-f]-1',10'-菲咯啉两种咪唑[4,5-f]-1',10'-菲咯啉衍生物, 并经过一、二维核磁共振谱以及质谱方法的验证. 利用1H NMR、质谱以及紫外可见分光光度法, 考察了以六～八元瓜环为主体, 咪唑[4,5-f]-1',10'-菲咯啉衍生物为客体的作用体系, 以及形成的主客体包结配合物的结构特征. 研究结果表明: 三种瓜环均与2-苯基-咪唑[4,5-f]-1',10'-菲咯啉发生相互作用, 客体以较小的苯基一端穿过瓜环内腔直至苯基部分和菲咯啉部分分别露置在瓜环的两个端口外, 特别是八元瓜环能容纳两个客体分子. 而对二甲氨基-2-苯基-咪唑[4,5-f]-1',10'-菲咯啉仅能与七及八元瓜环相互作用, 作用模式与前者相同.

关键词: 六～八元瓜环, 菲咯啉衍生物, 相互作用, 包结配合物

Two imidazo[4,5-f]-1',10'-phenathroline derivatives have been synthesized and characterized by using 1H NMR technique and mass spectroscopy methods. They are 2-phenylimidazo[4,5-f]-1',10'-phenathroline and 2-(p-dimethylaminophenyl)-2-phenylimidazo[4,5-f]-1',10'-phenathroline. Host-guest interac-tion of cucurbit[n]urils (n＝6～8) with the phenathroline derivatives has been investigated by NMR techniques, mass spectrum and UV absorption methods. The experimental results reveal that phenyl part of the guests penetrates the cavity of cucurbit[n]urils (n＝6～8) while phenyl and phenanthroline parts of the guests are located at the each port of a cucurbituril. Particularly, a cavity of cu-curbit[8]uril accommodates two of the guests.

Key words: phenanthroline derivative, interaction, host-guest complex, cucurbit[n]uril (n＝6～8)