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

doi:10.6023/cjoc202207004

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 326-331.DOI: 10.6023/cjoc202207004 Previous Articles Next Articles

NOTES

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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Abstract

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

Cite this article

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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Fig. & Tab. 10

Scheme 1. Synthetic route of probe L

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

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

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

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+

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.)

Figure 6. Job’s plot of L and Zn2+

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

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

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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一种具有聚集诱导发光性能的Zn2+荧光探针的设计合成