有机化学 ›› 2023, Vol. 43 ›› Issue (1): 326-331.DOI: 10.6023/cjoc202207004 上一篇    下一篇

研究简报

一种具有聚集诱导发光性能的Zn2+荧光探针的设计合成

张继东a,*(), 颜婉琳a, 胡文强a, 郭典a, 张大龙a, 权校昕a, 卜贤盼b, 陈思宇a   

  1. a 安康学院化学化工学院 陕西省富硒食品质量监督检验中心 陕西安康 725000
    b 中国富硒产业研究院 农业农村部富硒产品开发与质量控制重点实验室 陕西安康 725000
  • 收稿日期:2022-07-03 修回日期:2022-08-01 发布日期:2022-09-01
  • 通讯作者: 张继东
  • 基金资助:
    陕西省技术创新引导专项基金(2022QFY09-09); 陕西省重点研发计划(2020GY-246); 陕西省自然科学基金(S2018-JC-QN-0631); 陕西省教育厅专项科研计划(17JK0017); 陕西省教育厅专项科研计划(20JK0473); 农业农村部富硒产品开发国家地方联合工程实验室开放课题(Se-2020C04); 国家级大学生创新创业训练计划(S202111397012); 陕西省大学生创新创业训练计划(S202111397039)

Design and Synthesis of a Zn2+ Fluorescent Probe Based on Aggregation Induced Luminescence Properties

Jidong Zhanga(), Wanlin Yana, Wenqiang Hua, Dian Guoa, Dalong Zhanga, Xiaoxin Quana, Xianpan Bub, Siyu Chena   

  1. a Quality Supervision and Inspection Centre of Se-Enriched Food of Shaanxi Province, School of Chemistry & Chemical Engineering, Ankang University, Ankang, Shaanxi 725000
    b Key Laboratory of Se-Enriched Products Development and Quality Control of Ministry of Agriculture, Se-Enriched Products Research Institute of China, Ankang, Shaanxi 725000
  • Received:2022-07-03 Revised:2022-08-01 Published:2022-09-01
  • Contact: Jidong Zhang
  • Supported by:
    Shaanxi Provincial Technology Innovation Guidance Special Fund(2022QFY09-09); Shaanxi Province Key Research Program(2020GY-246); Natural Science Foundation of Shaanxi Province(S2018-JC-QN-0631); Special Scientific Research Project of Shaanxi Provincial Department of Education(17JK0017); Special Scientific Research Project of Shaanxi Provincial Department of Education(20JK0473); Key Laboratory of Se-Enriched Products Development and Quality Control, Ministry of Agriculture(Se-2020C04); National Undergraduate Training Program for Innovation and Entrepreneurship(S202111397012); Shaanxi Provincial Innovation Experiment Program for University Students(S202111397039)

以四苯乙烯为荧光基团, 5-叔丁基-2-羟基苯作为识别基团, 构建了一种新型的聚集诱导发光(AIE)效应Zn2+荧光探针L. 探针结构通过NMR和ESI-MS表征, 其荧光性能通过UV-vis和荧光光谱研究. 在乙醇/磷酸盐(PBS) (VV=7∶3, pH=7.4)溶液中, 探针对Zn2+表现出高灵敏度和选择性, 其检测限低至34.1 nmol•L–1, 在0~3.0×10–5 mol•L–1范围内, 探针对Zn2+表现出良好的线性关系. 在自然光和紫外灯下用肉眼观察到明显颜色变化, 可以实现Zn2+可视化检测. 通过Jobʼs plot, ESI-MS和密度泛函理论(DFT)理论计算对识别机理进行了研究. 报道的新型探针可作为分析测定Zn2+的一种便捷工具.

关键词: 四苯乙烯, 聚集诱导发光, 荧光探针, 锌离子

In this paper, a novel aggregation-induced emission (AIE) effect Zn2+ fluorescent probe L was constructed with aggregation-induced emission (AIE), tetraphenylethylene as the fluorescent group and 5-tert-butyl-2-hydroxybenzene as the recognition group. The structure of probe L was characterized by NMR and ESI-MS, and its fluorescence properties was studied by UV-vis and fluorescence spectroscopy. In ethanol/phosphate (PBS) (VV=7∶3, pH=7.4) solution, the probe L exhibited fluorescence-enhanced high selectivity and sensitivity detection of Zn2+, the detection limit was 34.1 nmol•L–1. In the range of 0~3.0×10–5 mol•L–1, the probe showed a good linear relationship to Zn2+. The obvious color change can be observed with the naked eye under UV light and natural light, which can realize the visual detection of Zn2+. The response mechanism of the probe to Zn2+ was studied by Job’s plot, ESI-MS and density functional theory (DFT) theoretical calculation. The novel probe reported in this paper can serve as a convenient tool for the analytical determination of Zn2+.

Key words: tetraphenylethyene, aggregation-induced emission (AIE), fluorescent probe, zinc ions