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化学学报
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化学学报 ›› 2004, Vol. 62 ›› Issue (18): 1811-1814. 上一篇    下一篇

研究论文

高选择性氟离子识别受体的设计与识别机理

郭琳, 张煊, 江云宝   

  1. 厦门大学化学系, 现代分析科学教育部重点实验室, 厦门, 361005
  • 投稿日期:2004-04-19 修回日期:2004-07-02 发布日期:2014-02-17
  • 通讯作者: 江云宝,E-mail:ybjiang@xmu.edu.cn;Tel/Fax:0592-2185662. E-mail:ybjiang@xmu.edu.cn
  • 基金资助:
    国家自然科学基金(No.20175020)、福建省自然科学基金(No.D0220001)、教育部优秀青年教师奖励计划(2001)和德国大众基金(No.I/77072)资助项目.

Design of a Fluoride-Selective Colorimetric Receptor and Its Fluoride Recognition Mechanism

GUO Lin, ZHANG Xuan, JIANG Yun-Bao   

  1. Department of Chemistry and the MOE Key Laboratory of Analytical Sciences, Xiamen University, Xiamen 361005
  • Received:2004-04-19 Revised:2004-07-02 Published:2014-02-17

PDF

472

被引次数

50

将酰胺识别基团耦合至基态具有分子内电荷转移特征的对硝基苯基偶氮苯胺分子中,设计合成了受体分子N-苯甲酰基4-(4'-硝基苯基偶氮基)苯胺(3),对氟离子表现出极高的识别选择性.乙腈中该受体3的最大吸收峰位于380 nm,加入氟离子后,该吸收峰强度逐渐减弱,同时在530 nm处出现新的吸收峰,后者为受体分子与氟离子形成的1:1配合物的吸收峰.溶剂极性效应实验表明,该吸收峰具有电荷转移特征.引入氟离子后受体3溶液的颜色由浅黄色转变为紫红色,可实现氟离子的裸眼检测.质子溶剂效应,1H NMR滴定为受体分子3与阴离子间的氢键作用本质提供了直接证据.

关键词: 偶氮苯, 氟离子, 阴离子识别, 电荷转移

This paper will report the design and synthesis of a fluoride-selective colorimetric receptor,N-benzoyl-4-(4'-nitrophenylazo)aniline, 3, in which amide as recognition group was coupled to 4-(4'-nitrophenylazo)aniline (2) of ground-state intramolecular charge transfer character. It was found that 3 had an absorption maximum at 380 nm in acetonitrile, which decreased gradually upon addition of F-. A new band peaked at 530 nm appeared, which turned the solution from light yellow to purplish red. The new band due to the hydrogen bonding complex of 3 with F- was shown to be of charge transfer character by the observation of a substantial red shift with increasing solvent polarity. 1H NMR titrations confirmed hydrogen bonding interaction between 3 and F-.

Key words: azobenzene, fluoride ion, anion recognition, charge transfer