高等学校化学学报

高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (06): 1239.doi: 10.3969/j.issn.0251-0790.2012.06.020

• 有机化学 • 上一篇    下一篇

1,10-邻菲啰啉并咪唑衍生物阴离子受体的合成及识别性能

陈华梅1, 岳凡1, 林海2, 林华宽3   

  1. 1. 新疆大学化学化工学院, 乌鲁木齐830046;
    2. 南开大学吸附与分离功能材料重点实验室, 天津 300071;
    3. 南开大学化学系, 天津 300071
  • 收稿日期:2011-07-06 出版日期:2012-06-10 发布日期:2012-06-10
  • 通讯作者: 陈华梅, 女, 博士, 副教授, 主要从事配位物理化学研究. E-mail: chen-hua-mei@163.com E-mail:chen-hua-mei@163.com
  • 基金资助:

    新疆维吾尔自治区自然科学基金(批准号: 2011211B06)和新疆大学自然科学基金(批准号: BS08011)资助.

Synthesis of Two Anion Receptors of 1H-Imidazo[4,5-f][1,10]phenanthroline Derivatives and Their Recognition Properties

CHEN Hua-Mei1, YUE Fan1, LIN Hai2, LIN Hua-Kuan3   

  1. 1. College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China;
    2. Key Laboratory of Functional Polymer Materials for Adsorption and Seperation,, Nankai University, Tianjin 300071, China;
    3. Department of Chemistry, Nankai University, Tianjin 300071, China
  • Received:2011-07-06 Online:2012-06-10 Published:2012-06-10

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被引次数

7

摘要： 设计合成了2个1,10-邻菲啰啉并咪唑衍生物阴离子受体2-(2-羟基苯基)-1H-咪唑[4,5-f][1,10]邻菲啰啉(1)和2-(2-羟基-5-溴苯基)-1H-咪唑[4,5-f][1,10]邻菲啰啉(2), 受体2的结构由X射线单晶衍射分析确证. 通过紫外-可见光谱滴定及 1H NMR滴定研究了这2个受体对F-, Cl-, Br-, I-, H2PO4-和AcO- 6种阴离子的识别传感作用及作用机理. 结果表明, 受体对AcO-, F-和H2PO4-有较强的传感作用, 溶液颜色由淡黄色变为黄色; 对Cl-的作用较弱; 而对Br-和I-则无明显作用. 通过机理研究发现, 受体与F-, H2PO4-和AcO-形成1: 1的氢键超分子, 当阴离子的量超过受体的1倍以后, 咪唑氮上的氢转移到阴离子; 受体与Cl-以氢键形成超分子复合物, 而与Br-和I-作用很弱.

关键词: 1,10-邻菲啰啉并咪唑衍生物, 晶体结构, 阴离子识别

Abstract: Anion play important roles in a wide range of chemical, biological and environmental processes. So anion binding and sensing became an active research field in supramolecular chemistry with potential applications in biomedical and environmental monitoring, anion exchange as well as anion transport. Artificial neutral receptors for anions are designed and synthesized in which color metric sensors are paid a good deal of attention for they could efficiently change their photo physical properties in the presence of anions. Imidazole and phenol are recently used in the design of neutral receptors for anions due to their ability to act as H-bond donors. Two anion receptors of 1H-imidazo[4,5-f][1,10]phenanthroline derivatives, 2-(2-hydroxyphenyl)-1H-imidazo[4,5-f][1,10]phenan-throline(1) and 2-(2-hydroxy-5-bromophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline(2) were designed and synthesized, and the structure of compound 2 was confirmed by single crystal X-ray diffraction analysis. Anion sensing and the mechanism studies were carried out by UV-Vis spectrophotometric titration and 1H NMR titration. The receptors exhibited sensing towards CH3COO-, F- and H2PO4- with color of the solution changed from pale yellow to yellow, and weakly sensing towards Cl- with inconspicuous response towards Br- and I- in DMSO. The receptors formed hydrogen bond supramolecular with anions F-, H2PO4- and CH3COO- as 1: 1 within[receptor]/[anion]=1. As flowed with the molar ratio exceeded 1, the proton of 1H-imidazo deprotoned and linked with the anion. The receptors formed hydrogen bond supramolecular with Cl-.

Key words: 1H-Imidazo[4,5-f][1,10]phenanthroline derivative, Crystal structure, Anion recognition

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