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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (01): 71-76. 上一篇    下一篇

研究论文

N-(2,4-二硝基苯基)-N -取代苯腙衍生物对阴离子识别研究

聂丽*,1,2，胡蕾1，傅绪成1，江云宝2   

  1. (1皖西学院化学系 六安 237012)
    (2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:2009-12-23 修回日期:2010-05-07 发布日期:2010-08-16
  • 通讯作者: 聂丽 E-mail:nieli@wxc.edu.cn
  • 基金资助:

    磁性介孔硅基质荧光探针研究及在重金属离子检测中应用

Synthesis of N-(2,4-Dinitrophenyl)-N -(substituted-phenyl)hydrazones and Their Anion Sensing

Nie Li*,1,2 Hu Lei1 Fu Xucheng1 Jiang Yunbao2   

  1. (1 Department of Chemistry, Wanxi College, Lu an 237012)
    (2 Department of Chemistry and the MOE Key Laboratory of Analytical Sciences, Xiamen University, Xiamen 361005)
  • Received:2009-12-23 Revised:2010-05-07 Published:2010-08-16

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合成了4种N-(2,4-二硝基苯基)-N -取代苯腙类阴离子结合受体(1～4, 取代基 R＝H, o-OCH3, o-Cl, o-OH), 应用紫外吸收光谱方法研究了其与阴离子的相互作用, 以及考察N -苯环取代基对受体分子之阴离子亲合力和选择性的影响. 实验显示: 乙腈中F－、CH3CO 等阴离子使受体分子吸收光谱红移, 溶液由黄色转变为红色, 其中受体分子2对 F－表现出高选择性的灵敏响应. 实验表明受体-阴离子间形成了氢键型超分子配合物, Job作图法给出了受体分子与阴离子的1∶1结合计量比, 1H NMR滴定为受体分子与阴离子间的氢键作用本质提供了直接证据.

关键词: N-(2,4-二硝基苯基)-N -苯腙, 阴离子识别, 氢键作用

Four N-(2,4-dinitrophenyl)-N -(substituted-phenyl)hydrazones (substituent R＝H, o-OCH3, o-Cl and o-OH) were synthesized as absorption spectral chemosensors for receptors. The binding properties of these receptors with anions such as F－ and AcO－ in CH3CN were investigated by UV-visible absorption spectroscopy. Results showed that a distinct color change occurred from yellow to light yellow upon addition of F－ and AcO－. Substituent was found to exert influence on the spectral response sensitivity and selectivity, with receptor 2 bearing an o-OCH3 substituent showing the highest selectivity and good sensitivity for F－. Job plots indicated a 1∶1 anion binding stoichiometry of the receptors, for which a hydrogen bonding interaction was identified from the 1H NMR titrations and the effect of competitive solvent MeOH on anion binding. As a distinct solution color change occurs it is possible to detect anions such as fluoride by naked eyes.

Key words: N-(2,4-dinitrophenyl)-N -phenylhydrazone, anion sensing, hydrogen bonding