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2013 , Vol. 33 >Issue 08: 1804 - 1809

DOI: https://doi.org/10.6023/cjoc201302008

研究论文

对叔丁基杯[4]芳烃-1,3-二取代邻菲罗啉衍生物的合成及对Ag+的识别作用

  • 李亮 ,
  • 戚伟光 ,
  • 王超 ,
  • 颜朝国
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  • a 上海应用技术学院化学与环境工程学院 上海 201418;
    b 扬州大学化学化工学院 扬州 225002

收稿日期: 2013-02-04

  修回日期: 2013-03-04

  网络出版日期: 2013-03-28

基金资助

国家自然科学基金(No. 20972132)资助项目.

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1,3-Disubstituted p-tert-Butylcalix[4]arene Derivatives Bearing Phenanthroline Moieties：Synthesis and Selective Recognition of Silver Ion

  • Li Liang ,
  • Qi Weiguang ,
  • Wang Chao ,
  • Yan Chaoguo
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  • a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
    b College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002

Received date: 2013-02-04

  Revised date: 2013-03-04

  Online published: 2013-03-28

Supported by

Project supported by the National Natural Science Foundation of China (No. 20972132).

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摘要

以对叔丁基杯[4]芳烃为母体, 首先通过两步烃基化反应合成出烷基桥联的氧代芳醛化合物, 接着与1,10-邻菲罗啉-5,6-二酮反应, 得到了邻菲罗啉为功能基团的杯芳烃衍生物. 化合物结构均用IR, NMR和ESI-HRMS进行了表征. 利用紫外可见吸收光谱, 详细研究了配体3c对金属离子的识别性能. 结果发现: 其对Ag+显示出优异的选择性, 并可以实现对Ag+的“裸眼”识别, 检测限达到5×10-6 mol/L.

关键词： 杯芳烃; 邻菲罗啉; 紫外吸收光谱; 离子识别

本文引用格式

李亮 , 戚伟光 , 王超 , 颜朝国 . 对叔丁基杯[4]芳烃-1,3-二取代邻菲罗啉衍生物的合成及对Ag+的识别作用[J]. 有机化学, 2013 , 33(08) : 1804 -1809 . DOI: 10.6023/cjoc201302008

Abstract

p-tert-Butylcalix[4]arene-1,3-dialdehydes were firstly obtained by two step alkylations of p-tert-butylcalix[4]arene with alkylene dihalide and hydroxyl-substituted benzaldehydes. Then p-tert-butylcalix[n]arene 1,3-disubstituted phenanthrolines were successfully prepared by condensation of active calixarene dialdehydes with 1,10-phenanthroline-5,6-dione. The structures of the prepared hoters were characterized with IR, NMR, and HRMS techniques. The recogination of calixarene 1,3-disubstituted phenanthroline for metal ions was studied with UV-Vis spectroscopy. A great affinity for Ag+ ions that can be clearly detected by naked eye was obtained.

Key words： calixarene; phenanthroline; UV spectroscopy; ion recognition

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