有机化学 ›› 2018, Vol. 38 ›› Issue (7): 1800-1805.DOI: 10.6023/cjoc201711002 上一篇    下一篇

所属专题: 荧光探针-生物传感合辑 有机超分子化学合辑

研究论文

基于功能化萘二甲酰亚胺席夫碱的Fe3+传感器分子的合成及性能

张有明, 韩冰冰, 林奇, 毛鹏鹏, 陈进发, 姚虹, 魏太保   

  1. 西北师范大学化学化工学院 兰州 730070
  • 收稿日期:2017-11-01 修回日期:2018-01-17 发布日期:2018-03-16
  • 通讯作者: 魏太保 E-mail:weitaibao@126.com
  • 基金资助:

    国家自然科学基金(Nos.21662031,21661028,21574104,21262032)资助项目.

Synthesis and Fe3+ Sensing Properties of the Chemosensor Based on Functionalized Naphthalimide Schiff Base Derivative

Zhang Youming, Han Bingbing, Lin Qi, Mao Pengpeng, Chen Jinfa, Yao Hong, Wei Taibao   

  1. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
  • Received:2017-11-01 Revised:2018-01-17 Published:2018-03-16
  • Contact: 10.6023/cjoc201711002 E-mail:weitaibao@126.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21662031, 21661028, 21574104, 21262032).

将功能化的1,8-萘二甲酰亚胺衍生物与羟基萘甲醛缩合,合成了一种新颖的传感器分子2-羟基-1-奈甲醛缩N-(4-氨基苯基)-1,8-奈二甲酰胺席夫碱(H1).通过核磁共振氢谱,碳谱和高分辨质谱等方法对H1进行了表征.测定了H1在二甲基亚砜(DMSO)/H2O(VV=7∶3)溶液中的荧光光谱,其最大荧光发射波长为496 nm.H1的溶液在365 nm紫外灯照射下显示黄绿色荧光.H1对Fe3+具有荧光-比色双通道检测能力.当在H1的DMSO/H2O溶液中分别加入Fe3+,Ag+,Ca2+,Ba2+,Co2+,Ni2+,Cd2+,Pb2+,Zn2+,Cu2+,Mg2+和Hg2+等阳离子时,只有Fe3+的加入使H1的荧光猝灭并且溶液颜色褪色.抗干扰实验结果表明,这一识别过程不受其它阳离子干扰.H1对Fe3+具有较高的检测灵敏度,对Fe3+的荧光光谱最低检测限和紫外-可见吸收光谱最低检测限分别为3.04×10-8和2.71×10-6 mol·L-1.最后,制备了基于H1的检测试纸,该试纸可以方便快捷地检测水中的Fe3+.

关键词: 萘二甲酰亚胺衍生物, 席夫碱, 传感器分子, 荧光-比色双通道识别, Fe3+

A novel sensor molecule 2-hydroxyl-1-naldehyde-N-(4-aminophenyl)-1,8-naphthalimide (H1) based on functionalized naphthalimide Schiff Base derivative was synthesized. H1 was characterized by 1H NMR, 13C NMR and HRMS. Furthermore, its fluorescence properties were studied in dimethyl sulfoxide (DMSO)/H2O (V:V=7:3) solutions. Its maximum emission wavelength was 496 nm. The solution of H1 has yellow-green fluorescence under the UV lamp (365 nm). H1 showed fluorescence-colorimetric dual channel identification ability for Fe3+. With the addition of various metal ions into the H1 solution, only Fe3+ caused the fluorescence of the H1 quenching and the color disappeared. Other cations such as Ag+, Ca2+, Ba2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cu2+, Mg2+ and Hg2+ could not induce similar response. The results of anti-disturbance experiment demonstrated that other cations can not interfere in the detection of Fe3+. H1 has good sensitivity for Fe3+, the fluorescence and UV-Vis detection limits of the H1 for Fe3+ are 3.04×10-8 and 2.71×10-6 mol·L-1, respectively. Finally, the test strips based on the H1 were prepared, which could conveniently and efficiently detect Fe3+ in water.

Key words: naphthalimide derivative, Schiff base, sensor molecule, fluorescence-colorimetric dual channel identification, Fe3+