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化学学报
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化学学报 ›› 2006, Vol. 64 ›› Issue (1): 79-84. 上一篇    下一篇

研究论文

缩氨基硫脲衍生物受体的合成及阴离子识别研究

张有明，徐维霞，周艳青，姚虹，魏太保*   

  1. (西北师范大学化学化工学院 甘肃省高分子材料重点实验室 兰州 730070)
  • 投稿日期:2005-04-13 修回日期:2005-09-20 发布日期:2006-01-14
  • 通讯作者: 魏太保

Synthesis of Thiosemicarbazone Derivative Receptors and Their Anion Recognition Properties

ZHANG You-Ming, XU Wei-Xia, ZHOU Yan-Qing, YAO Hong, WEI Tai-Bao*   

  1. (Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering,
    Northwest Normal University, Lanzhou 730070)
  • Received:2005-04-13 Revised:2005-09-20 Published:2006-01-14
  • Contact: WEI Tai-Bao

PDF

1556

被引次数

106

利用简便的方法设计合成了三种缩氨基硫脲衍生物受体分子. 利用紫外-可见吸收光谱及1H NMR考察了其与 F－, Cl－, Br－, I－, CH3COO－, C3H7COO－, ClO4－, NO3－等阴离子的作用. 结果表明, 该类受体分子与阴离子形成氢键配合物, 加入F－, CH3COO－, C3H7COO－时, 溶液颜色由无色转变为黄色, 而加入其它阴离子则无变化, 从而实现对这三种阴离子的裸眼检测. 通过计算可知, 同种受体分子对此三种阴离子的作用为F－＞C3H7COO－＞CH3COO－. 随着苯环上取代基的变化, 此三种受体分子对三种阴离子的作用呈现出有规律的变化, 即o-F取代的受体分子对阴离子的识别作用大于其它两种受体分子, 且主客体间形成1∶1的配合物. 1H NMR滴定及质子溶剂效应为受体分子与阴离子间的氢键作用本质提供了直接依据.

关键词: 缩氨基硫脲, 合成, 阴离子识别

Three unknown neutral thiosemicarbazone derivative receptors were synthesized in good yields. The binding properties of the receptors with anions such as F－, Cl－, Br－, I－, CH3COO－, C3H7COO－, ClO4－ and NO3－ in acetonitrile were examined by UV-Vis and 1H NMR spectroscopy methods. A clear color change was observed from colorless to light yellow upon addition of F－, CH3COO－ or C3H7COO－ to the solution of the three receptors in acetonitrile. The results showed that the three receptors had a better selectivity to F－, CH3COO－ and C3H7COO－, but no evident binding with Cl－, Br－, I－, ClO4－ and NO3－, and the association constants followed the trend: F－＞C3H7COO－＞CH3COO－, while regularly the three receptors had different binding ability with the three anions because of the electronic effect. The UV-Vis data indicated that a 1∶1 stoichiometry complex was formed between compounds 3a, 3b, 3c and anions, while 1H NMR titrations confirmed hydrogen interaction between the receptors and anions.

Key words: thiosemicarbazone, synthesis, anion recognition