一种具有聚集诱导发光性能的Zn2+荧光探针的设计合成

doi:10.6023/cjoc202207004

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

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 Zhang^a(), Wanlin Yan^a, Wenqiang Hu^a, Dian Guo^a, Dalong Zhang^a, Xiaoxin Quan^a, Xianpan Bu^b, Siyu Chen^a

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)

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摘要/Abstract

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) (V∶V=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) (V∶V=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

引用此文

张继东, 颜婉琳, 胡文强, 郭典, 张大龙, 权校昕, 卜贤盼, 陈思宇. 一种具有聚集诱导发光性能的Zn²⁺荧光探针的设计合成[J]. 有机化学, 2023, 43(1): 326-331.

Jidong Zhang, Wanlin Yan, Wenqiang Hu, Dian Guo, Dalong Zhang, Xiaoxin Quan, Xianpan Bu, Siyu Chen. Design and Synthesis of a Zn²⁺ Fluorescent Probe Based on Aggregation Induced Luminescence Properties[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 326-331.

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图/表 10

图式1. 探针L的合成路线

Scheme 1. Synthetic route of probe L

图1. (a) L在不同水分比例的THF/H2O (10 μmol?L–1)中的荧光发射光谱(激发波长为 400 nm)以及(b) L在THF/H2O中荧光强度变化趋势图

Figure 1. (a) Fluorescence emission spectra of L in THF/H2O with different water fractions (10 μmol?L–1) (excitation wavelength is 400 nm), and (b) plot of emission intensities of L in THF/H2O versus water contents

图2. 探针L (10 μmol?L–1)与不同金属离子作用的荧光发射光谱

Figure 2. Fluorescence emission spectra of the fluorescence probe L (10 μmol?L–1) interacting with different metal ions Insert: photograph of L and L+Zn2+ under a 365 nm UV lamp

图3. 探针L(10 μmol?L–1)和L+Zn2+(10 μmol?L–1)在乙醇/磷酸盐(PBS) (V∶V=7∶3, pH=7.4)混合溶液中的紫外光谱

Figure 3. UV-vis absorption spectra of L (10 μmol?L–1) and L+Zn2+(10 μmol?L–1) in methanol solutions Insert: photograph of L and L+Zn2+ under visible light

图4. 在其它金属离子存在下在探针L乙醇/磷酸盐(PBS) (V∶V=7∶3, pH=7.4)混合溶液中加入Zn2+前后在548 nm处的荧光强度的变化

Figure 4. Emission intensity changes of L (10 μmol?L–1) in EtOH/PBS (V∶V=7∶3, pH=7.4) solution with Zn2+(50 μmol?L–1) and other cations(50 μmol?L–1) 1: Zn2+; 2: Na++Zn2+; 3: K++Zn2+; 4: Ag++Zn2+; 5: Mg2++Zn2+; 6: Al3++Zn2+; 7: Cr3++Zn2+; 8: Mn2++Zn2+; 9: Fe2++Zn2+; 10: Fe3++Zn2+; 11: Co2++Zn2+; 12: Ni2++Zn2+; 13: Cu2++Zn2+; 14: Ca2++ Zn2+; 15: Cd2++Zn2+; 16: Ba2++Zn2+; 17: Hg2++Zn2+; 18: Pb2++Zn2+

图5. (a)探针L(10 μmol?L–1)在乙醇/磷酸盐(PBS) (V∶V=7∶3, pH=7.4)对不同浓度的Zn2+ (0~3.0 equiv.)的荧光光谱图, 以及(b)探针L (10 μmol?L–1)在548 nm处荧光强度对不同 Zn2+浓度的线性图(0~3.0 equiv.)

Figure 5. (a) Fluorescence probe spectra of 10 μmol?L–1 L in C2H5OH/PBS (V∶V=7∶3, pH=7.4) solution in the presence of Zn2+, and (b) the fluorescence intensity at 548 nm of probe L(10 μmol?L–1) upon addition of different concentrations of Zn2+(0~3.0 equiv.)

图6. 探针L和Zn2+的Job’s plot曲线图

Figure 6. Job’s plot of L and Zn2+

图式2. 探针L识别Zn2+的荧光增强机理

Scheme 2. Fluorescence enhancement mechanism for L to recognize Zn2+

图7. DFT理论计算的L和L-Zn2+的HOMO/LUMO能量轨道

Figure 7. Optimized structures and HOMO/LUMO of L and complex L-Zn2+ by DFT calculation

图8. (a, c) L及(b, d) L与Zn2+形成的配合物的SEM图像

Figure 8. SEM images of (a, c) L and (b, d) their complex with ZnCl2.

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一种具有聚集诱导发光性能的Zn²⁺荧光探针的设计合成

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

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