有机化学 ›› 2014, Vol. 34 ›› Issue (8): 1623-1629.DOI: 10.6023/cjoc201403024 上一篇    下一篇

研究论文

可检测Zn2+,Cd2+和Cu2+的氮杂香豆素荧光探针的合成及性能研究

樊江莉, 徐群利, 朱浩, 彭孝军   

  1. 大连理工大学精细国家重点实验室 大连 116024
  • 收稿日期:2014-03-11 修回日期:2014-04-04 出版日期:2014-08-25 发布日期:2014-04-18
  • 通讯作者: 樊江莉 E-mail:fanjl@dlut.edu.cn
  • 基金资助:

    国家自然科学基金(No.21136002)、教育部新世纪优秀人才支持计划(No.NCET-12-0080)和辽宁省自然科学基金(No.2013020115)资助项目.

Synthesis and Properties of an Aza-coumarin Based Sensor for Detection of Zn2+, Cd2+ and Cu2+

Fan Jiangli, Xu Qunli, Zhu Hao, Peng Xiaojun   

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024
  • Received:2014-03-11 Revised:2014-04-04 Online:2014-08-25 Published:2014-04-18
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21136002), the Program for New Century Excellent Talents in University (No. NCET-12-0080) and the Natural Science Foundation of Liaoning Province (No. 2013020115).

通过3-甲酰基-7-NN-二甲基氮杂香豆素(T1)与氨甲基吡啶的缩合反应,生成一个缩醛胺结构化合物NC-1而非席夫碱. 通过对比产物分子NC-2NC-4和结构优化计算研究了该反应的机理,确定了分子内氢键在反应中的稳定作用. 光谱测试结果表明,NC-1能够分别与Zn2+,Cd2+和 Cu2+作用,产生不同的荧光和吸收光谱变化,现象肉眼可见.

关键词: 氮杂香豆素, 席夫碱, 合成机理, 荧光探针

By condensation of 7-(dimethylamino)-2-oxo-2H-benzo[b][1,4]oxazine-3-carbaldehyde (T1) and 2-aminomethyl- pyridine, an aminal NC-1 rather than a Schiff base was synthesized. The synthetic mechanism was likely to be determined by stabilizing effect of intramolecular hydrogen bond, which was proved through density functional theory (DFT) calculations and control molecules NC-2NC-4. Furthermore, the spectroscopic tests indicated that NC-1 behaves as a fluorescent probe for sensing Cd2+, Zn2+ and Cu2+ by different fluorescence and color changes which can be observed by naked eyes.

Key words: aza-coumarin, Schiff base, synthesis mechanism, fluorescent probe