中华医学超声杂志

应用化学 ›› 2011, Vol. 28 ›› Issue (04): 464-470.DOI: 10.3724/SP.J.1095.2011.00340

• 研究论文 • 上一篇    下一篇

吡啶基咪唑[4,5-f]1,10-菲咯啉合成、表征及与瓜环作用的光谱学考察

黄智文,林友文*,李光文   

  1. (福建医科大学药学院 福州 350004)
  • 收稿日期:2010-06-11 修回日期:2010-09-02 出版日期:2011-04-10 发布日期:2011-04-10
  • 通讯作者: 林友文，教授; Tel/Fax:0591-22862016; E-mail:linhumor@sina.com; 研究方向：生物医用材料
  • 基金资助:
    福建医科大学教授学术发展基金计划（JS09004）资助项目

Synthesis , Characterization of Pyridylimidazo[4,5-f]1,10-phenanthroline Derivates and Spectroscopic Study Their Interaction With Cucurbit[n]urils

HUANG Zhiwen, LIN Youwen*, LI Guangwen   

  1. (College of Pharmacy,Fujian Medical University,Fuzhou 350004)
  • Received:2010-06-11 Revised:2010-09-02 Published:2011-04-10 Online:2011-04-10
  • Contact: YouWen Lin

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摘要：

设计合成了2个吡啶基菲咯啉衍生物2-(3-吡啶基)咪唑[4,5-f]1,10-菲咯啉(G1)和2-(4-吡啶基)咪唑[4,5-f]1,10-菲咯啉(G2)，通过元素分析、质谱和核磁共振氢谱对其结构进行了表征。 利用紫外吸收光谱和荧光光谱法考察了所合成化合物与六元瓜环Q[6]、七元瓜环Q[7]的相互作用，以及体系pH值对主-客体相互作用的影响。 在酸性条件下，Q[6]、Q[7]与Gl以及Q[6]与G2均发生包合形成1∶1的包合物，并有荧光增敏作用；Q[7]与G2作用形成1∶2包合物，且对G2有荧光猝灭作用；Q[6]、Q[7]与G1的包合常数分别为3.00×104和1.86×104 L/mol；Q[6]、Q[7]与G2的包合常数分别为1.64×104和1.01×103 L/mol。 随着体系酸性减弱，瓜环与客体作用减弱，在中性条件下，瓜环未与客体发生包合作用。

关键词: 菲咯啉衍生物, 合成, 瓜环, 主客体包合作用, 光谱法

Abstract:

Two pyridyl imidazo[4,5-f]1,10-phenanthroline derivates, namely 2-(3-pyridyl)-imidazo[4,5-f]1,10-phenanthroline(G1) and 2-(4-pyridyl)imidazo [4,5-f]1,10-phenanthroline(G2), were synthesized and characterized by elemental analysis, 1H NMR and MS. Under various concentrations of cucurbit[n]urils(Q[n], n=6,7), the interaction of Q[n] with G1 and G2 were studied in buffer solutions with different pH values by using UV-Vis spectroscopy and fluorescence spectrophotometry. The results revealed that cucurbit[n]urils(n=6,7) form a 1∶1 complex with G1, and Q[6] form a 1∶1 complex with G2 in acidic solution, fluorescent sensitizing effects of both Q[6] and Q[7] toward guests were determined. Under acidic solution Q[7] formed a 2∶1 complex with G2, and a fluorescent quenching effect of Q[7] on G2 was observed. Association constants(K) of Q[n](n=6,7) with G1 were found to be 3.00×104 L/mol, 1.86×104 L/mol respectively, while those of Q[n](n=6,7) with G2 are 1.64×104 L/mol and 1.01×103 L/mol respectively. With decreasing acidity of the systems, the interaction between guests and Q[n](n=6,7) weakened and no interaction was observed under neutral conditions.

Key words: phenanthroline derivates, synthesis, Cucurbit[n]urils, Rost-guest inclusion reaction, Spectroscopic method

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