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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (11): 1864-1869. 上一篇    下一篇

研究论文

基于多重氢键组装的双杯冠合成及对铯离子的络合

金永东，刘云，杨永安，张东，但贵萍，杜鹃，袁立华，冯文*   

  1. (1辐射物理与技术教育部重点实验室 四川大学化学学院 原子核科学技术研究所 成都 610064)
    (2中国工程物理研究院核物理与化学研究所 绵阳 621900)
  • 收稿日期:2011-02-22 修回日期:2011-05-14 发布日期:2011-06-21
  • 通讯作者: 冯文 E-mail:wfeng9510@scu.edu.cn

Synthesis of a Bis-calixcrown Based on Multiple Hydrogen Bonds and Complexation towards Cesium Ion

JIN Yong-Dong, LIU Yun, YANG Yong-An, ZHANG Dong, DAN Gui-Ping, DU Juan, YUAN Li-Hua, FENG Wen   

  1. (1 Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chem-istry, Institute of Nuclear Science and Technology, Sichuan University, Chengdu 610064)
    (2 Institute of Nuclear Physics and Chemistry, China Academy of Engineering Physics, Mianyang 621900)
  • Received:2011-02-22 Revised:2011-05-14 Published:2011-06-21

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合成了一种基于多重氢键组装形成的新型双杯冠化合物, 利用核磁共振氢谱(1H NMR)和碳谱(13C NMR)以及高分辨质谱(ESI-HRMS)对组装前体分子结构进行了表征. 通过一维和二维核磁共振氢谱(2D NOESY)研究了该双杯冠的的自组装结构, 并采用核磁共振和紫外-可见光谱的方法测定了其对铯离子的络合. 实验表明, 通过氢键组装形成的双杯冠化合物, 由于阻止了单杯冠分子内组装而限制了冠醚环构象改变, 其萃取率由单杯冠的82%提高到96%.

关键词: 双杯冠, 自组装, 氢键, 络合, 铯离子

A novel bis-calixcrown formed by multiple hydrogen bonds was reported in this paper. Its structure was characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, carbon-13 nuclear magnetic resonance (13C NMR) spectroscopy, and high-resolution mass spectrometry (ESI-HRMS). The self-assembly structure was investigated by one- and two-dimension nuclear magnetic resonance (2D NOESY) spectra. The complexation towards cesium ions was examined by 1H NMR and UV-vis spectra. The results demonstrated that the bis-calixcrown assembled through multiple hydrogen bonds provided an increased extractability of 96% compared to that of 84% for the mono-calixcrown. This is attributed to the outcome of the limited conformational change of the crown ring that results from the blocking of intramolecular self-assembly of the mono-calixcrown.

Key words: bis-calixcrown, self-assembly, hydrogen bond, complex, cesium ion