有机化学 ›› 2018, Vol. 38 ›› Issue (11): 3026-3031.DOI: 10.6023/cjoc201804041 上一篇    下一篇

所属专题: 荧光探针-生物传感合辑 有机小分子-金属协同催化

研究论文

水介质中基于咔唑-席夫碱水解反应检测HSO4的比色和荧光探针

李英俊a, 张楠a, 刘季红b, 靳焜c, 王思远a   

  1. a 辽宁师范大学化学化工学院 大连 116029;
    b 大连理工大学化环生学部分析测试中心 大连 116023;
    c 大连理工大学精细化工国家重点实验室 大连 116012
  • 收稿日期:2018-04-22 修回日期:2018-06-22 发布日期:2018-07-16
  • 通讯作者: 李英俊 E-mail:chemlab.lnnu@163.com
  • 基金资助:

    辽宁省自然科学基金(No.20102126)资助项目.

Detection of HSO4- Ion with a Colorimetric and Fluorescent Probe Based on Hydrolysis Reaction of Carbazole-Derived Schiff Base in Aqueous Medium

Li Yingjuna, Zhang Nana, Liu Jihongb, Jin Kunc, Wang Siyuana   

  1. a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b Chemistry Analysis & Research Center, Faculty of Chemical, Environmental & Biological Science and Technology, Dalian University of Technology, Dalian 116023;
    c State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012
  • Received:2018-04-22 Revised:2018-06-22 Published:2018-07-16
  • Supported by:

    Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

合成出了1个新型基于咔唑的席夫碱衍生物L,评价了其在水性介质中选择性检测HSO4-离子的性能.在CH3CN-H2O(VV=9:1)中,N-(9-乙基-咔唑-3-基)-1-甲基-1-(4-硝基苯基)甲亚胺(L)通过席夫碱的水解反应,能够选择性地识别HSO4-离子,并引起从橙色到无色明显的视觉颜色变化;在紫外灯下,显示出蓝色荧光.在其它阴离子存在下,由HSO4-离子引起的荧光增强现象没有受到影响.通过Job曲线、1H NMR滴定光谱和HRMS谱研究了探针L检测HSO4-的机理.探针L对HSO4-离子的检出限为1.91×10-8mol·L-1.化合物L是HSO4-的高选择性、高灵敏度的比色和荧光增强型探针.

关键词: HSO4-, 咔唑, 席夫碱, 比色, 荧光, 水解

A novel carbazole-based Schiff base derivative L was synthesized and evaluated for the property of selective detection of HSO4- ion in aqueous medium. N-(9-Ethyl-carbazol-3-yl)-1-methyl-1-(4-nitrophenyl)-methanimine (L) selectively recognized HSO4- ion in CH3CN-H2O (V:V=9:1) via the hydrolysis reaction of Schiff bases to elicit a distinct visual colour change from orange to colorless with a significant blue fluorescence under the UV lamp. The fluorescence enhancement phenomenon caused by HSO4- ion did not change in the presence of other anions. The sensing mechanism of probe L for HSO4- had been investigated by Job's plot, 1H NMR titration spectra and HRMS spectrum. The detection limit for the HSO4- ion was determined as 1.91×10-8mol·L-1. The compound L can be used as a highly selective and sensitive colorimetric, and fluorescent turn-on probe for HSO4-.

Key words: HSO4-, carbazole, Schiff base, colorimetric, fluorescent, hydrolysis