基于聚集诱导效应(AIE)-激发态分子内质子转移(ESIPT)效应的四苯乙烯荧光探针对Zn(II)检测研究

doi:10.6023/cjoc202307021

有机化学 ›› 2024, Vol. 44 ›› Issue (4): 1337-1342.DOI: 10.6023/cjoc202307021 上一篇下一篇

研究论文

基于聚集诱导效应(AIE)-激发态分子内质子转移(ESIPT)效应的四苯乙烯荧光探针对Zn(II)检测研究

张继东^a^,^b^,^*(), 杨垚^a, 张杰^a, 厍伟^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:2023-07-21 修回日期:2023-10-15 发布日期:2023-11-15
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(2023YBGY-152); 陕西省教育厅专项科研计划项目(23JK0274); 安康学院科研项目重点项目(2021AYZD03); 国家级大学生创新创业训练计划(202211397014); 陕西省大学生创新创业训练计划(S202211397031)

Detection of Zn(II) by Tetraphenylethyene Fluorescent Probe Based on Aggregation-Induced Emission (AIE)-Excited State Intramolecular Proton Transfer (ESIPT) Effect

Jidong Zhang^a^,^b(), Yao Yang^a, Jie Zhang^a, Wei She^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:2023-07-21 Revised:2023-10-15 Published:2023-11-15
Contact: * E-mail: akuzjd@aku.edu.cn
Supported by:
Shaanxi Provincial Technology Innovation Guidance Special Fund(2022QFY09-09); Shaanxi Provincial Key Research Program(2023YBGY-152); Shaanxi Provincial Education Department Special Scientific Research Project(23JK0274); Key Natural Science Research Project of Ankang University(2021AYZD03); National Undergraduate Training Program for Innovation and Entrepreneurship(202211397014); Shaanxi Provincial Innovation Experiment Program for University Students(S202211397031)

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摘要/Abstract

设计合成了一种以四苯乙烯为荧光基团、邻香草醛为识别基团的聚集诱导效应(AIE) Zn²⁺荧光探针. 探针的结构通过¹H NMR、质谱及X射线单晶衍射进行了表征. 荧光光谱研究发现, 探针对Zn²⁺表现出良好的选择性和灵敏性, 荧光强度随着Zn²⁺的浓度增大而逐渐增强. 通过Job plot和单晶结构表征发现, 探针与Zn²⁺是2∶1的结合模式, 检测限为56.2 nmol•L^–1. 检测机理归因于激发态分子内质子转移(ESIPT)和AIE效应. 该新型AIE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, 锌配合物

A aggregation induced effect (AIE) Zn²⁺ fluorescence probe with tetrastyrene as the fluorescent group and orthovanillin as the recognition group was designed and synthesized. The structure of the probe was characterized by ¹H NMR, MS and single-crystal X ray diffraction. The fluorescence spectra showed that the probe has good selectivity and sensitivity to Zn²⁺, and its fluorescence enhances with the increase of concentration of Zn²⁺. Through job plot and single crystal structure characterization, it was found that the probe has a 2∶1 binding mode with Zn²⁺, and the detection limit is 56.2 nmol•L^–1. The detection mechanism was attributed to the excited state intramolecular proton transfer (ESIPT) and AIE effect. The new AIE probe can be used as a convenient tool for the analysis and determination of Zn²⁺.

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

引用此文

张继东, 杨垚, 张杰, 厍伟. 基于聚集诱导效应(AIE)-激发态分子内质子转移(ESIPT)效应的四苯乙烯荧光探针对Zn(II)检测研究[J]. 有机化学, 2024, 44(4): 1337-1342.

Jidong Zhang, Yao Yang, Jie Zhang, Wei She. Detection of Zn(II) by Tetraphenylethyene Fluorescent Probe Based on Aggregation-Induced Emission (AIE)-Excited State Intramolecular Proton Transfer (ESIPT) Effect[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1337-1342.

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图/表 9

图式1. 化合物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(激发波发射光谱长为395 nm)以及(b) L在THF溶液中随不同水含量的荧光值图

Figure 1. (a) Fluorescence emission spectra of L in THF/H2O with different water fractions (10 μmol?L–1) (excitation wavelength is 395 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(插图: 365 nm紫外灯下L和L+Zn2+的照片)

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 mol?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(插图: 可见光下L和L+Zn2+的照片)

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

图4. L(10 μmol?L–1)在乙醇/PBS (V∶V=7∶3, pH=7.4)与Zn2+ (50 μmol?L–1)和其它阳离子(50 μmol?L–1)作用后的发射强度变化

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: L, 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)不同浓度的Zn2+ (0~5.0×10–5 mol?L–1)时探针L (10 μmol? L–1)在乙醇/PBS (V∶V=7∶3, pH=7.4)中的荧光光谱图以及(b)探针L (10 μmol?L–1)中加入不同Zn2+ (0~ 5.0×10–5 mol?L–1)浓度后在583 nm处荧光强度

Figure 5. (a) Fluorescence probe spectra of L (10 μmol?L–1) in C2H5OH/PBS (V∶V=7∶3, pH=7.4) solution in the presence of Zn2+ (0~5.0×10–5 mol?L–1), and (b) the fluorescence intensity at 583 nm of probe L (10 μmol?L–1) upon addition of different concentrations of Zn2+ (0~5.0×10–5 mol?L–1)

图6. 探针L和Zn2+的Job plot曲线图

Figure 6. Job plot of L and Zn2+

图7. 配合物ZnL2的单晶结构

Figure 7. Crystal structure of the complex ZnL2

图8. (a, c) L及(b, d)配合物ZnL2的SEM图像

Figure 8. SEM images of (a, c) L and (b, d) complex ZnL2

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基于聚集诱导效应(AIE)-激发态分子内质子转移(ESIPT)效应的四苯乙烯荧光探针对Zn(II)检测研究

Detection of Zn(II) by Tetraphenylethyene Fluorescent Probe Based on Aggregation-Induced Emission (AIE)-Excited State Intramolecular Proton Transfer (ESIPT) Effect

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