高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (7): 1397-1404.doi: 10.7503/cjcu20190159

• 有机化学 • 上一篇    下一篇

苯并噻唑类荧光探针的合成及对N2H4·H2O和HSO3-的检测性能

王金金1,2, 戚少龙1,3, 杜建时3, 杨清彪1(), 宋岩2, 李耀先1   

  1. 1. 吉林大学化学学院, 长春 130021
    2. 吉林化工学院材料科学与工程学院, 吉林 132022
    3. 吉林省淋巴外科重点实验室, 吉林大学中日联谊医院, 长春 130031
  • 收稿日期:2019-03-18 出版日期:2019-05-24 发布日期:2019-07-09
  • 作者简介:

    杨清彪, 男, 博士, 教授, 主要从事有机合成与功能材料研究. E-mail: yangqb@jlu.edu.cn

  • 基金资助:
    吉林省自然科学基金(批准号: 20160101311JC, 20170101105JC)、 吉林省科技厅重点项目(批准号: 20170204039GX)和吉林市科技局项目(批准号: 20161204)资助.

Synthesis of Benzothiazole Fluorescent Probe for Detection of N2H4·H2O and HSO3-

WANG Jinjin1,2, QI Shaolong1,3, DU Jianshi3, YANG Qingbiao1,*(), SONG Yan2, LI Yaoxian1   

  1. 1. College of Chemistry, Jilin University, Changchun 130021, China
    2. College of Materials Science and Engineering, Jilin Institute of Chemical Technology, Jilin 132022, China
    3. Jilin Provincial Key Laboratory of Lymphatic Surgery, China-Japan Union Hospital of Jilin University,Changchun 130031, China
  • Received:2019-03-18 Online:2019-05-24 Published:2019-07-09
  • Contact: YANG Qingbiao E-mail:yangqb@jlu.edu.cn
  • Supported by:
    † Supported by the Natural Science Foundation of Jilin Province, China(Nos.20160101311JC, 20170101105JC), the Science Technology Department Key Project of Jilin Province, China(No.20170204039GX) and the Science and Technology Bureau Project of Jilin City, China(No.20161204).

摘要:

以苯并噻唑为荧光团, 氰基乙酸乙酯为识别基团, 设计合成了对水合肼和亚硫酸氢盐具有双重检测能力的荧光探针3-(2-羟基-苯并噻唑)-2-氰基-丙烯酸乙酯(HBT-CN). 在二甲基亚砜/磷酸盐(体积比为1:4)的缓冲液中, 探针对水合肼和亚硫酸氢盐具有良好的选择性, 且荧光强度分别增强了5.6倍(500 nm)和7.5倍(458 nm). 结果表明, 在检测过程中, HTB-CN与水合肼发生了还原-缩合反应, 生成了醛腙, 在波长500 nm处发出黄绿色的荧光信号; HBT-CN与亚硫酸氢盐发生了亲核加成反应, 在波长458 nm处发出蓝色的荧光信号, 从而实现了对水合肼和亚硫酸氢盐的差异性定性与定量检测.

关键词: 荧光探针, 苯并噻唑衍生物, 水合肼, 亚硫酸氢盐

Abstract:

Based on benzothiazole as fluorophore, ethyl cyanoacetate as recognition group, a new fluorescent probe 3-(2-hydroxy-benzothiazole)-2-cyano-ethyl acrylate(HBT-CN) with dual detection ability for hydrazine hydrate and bisulfite was designed and synthesized. In DMSO/PBS(1:4, volume ratio) buffered condition, the probe displayed good selectivity towards hydrazine and bisulfite with approximate 5.6 times(500 nm) and 7.5 times(458 nm) fluorescence enhancement at 500 and 458 nm, respectively. 1H NMR, 13C NMR and HRMS results showed that during the detection process, HBT-CN undergoed a reduction-condensation reaction with N2H4·H2O, which form a aldehyde hydrazone and emited pale yellow fluorescent signal at 500 nm. And HBT-CN under went a nucleophilic addition reaction with bisulfite and emited blue fluorescent signal at 458 nm. So, differential qualitative and quantitative detection of N2H4·H2O and HSO3- can be achieved.

Key words: Fluorescent probe, Benzothiazole, Hydrazine hydrate, Bisulfite

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