Synthesis of Tetraphenylethylene Based Amides for Detection of Copper(II) Ion with High Sensitivity and Selectivity

doi:10.6023/cjoc202403043

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2581-2587.DOI: 10.6023/cjoc202403043 Previous Articles Next Articles

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四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu^2＋

苏小龙, 李健鹏, 刘孟鑫, 邹莉, 杨得锁^*(), 冯海涛^*()

宝鸡文理学院化学化工学院聚集诱导发光研究中心陕西宝鸡 721000

收稿日期:2024-03-27 修回日期:2024-05-23 发布日期:2024-06-07
基金资助:
国家自然科学基金(52173152); 国家自然科学基金(21805002); 陕西省科技创新团队(2022TD-36); 陕西省自然科学基金(2024JC-YBMS-123); 陕西省教育厅服务地方(23JC001)

Synthesis of Tetraphenylethylene Based Amides for Detection of Copper(II) Ion with High Sensitivity and Selectivity

Xiaolong Su, Jianpeng Li, Mengxin Liu, Li Zou, Desuo Yang^*(), Haitao Feng^*()

Aggregation-Induced Emission Research Center, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721000

Received:2024-03-27 Revised:2024-05-23 Published:2024-06-07
Contact: *E-mail: yangdesuo@163.com; haitaofeng907@163.com
Supported by:
National Natural Science Foundation of China(52173152); National Natural Science Foundation of China(21805002); Scientific and Technological Innovation Team of Shaanxi Province(2022TD-36); Natural Science Foundation of Shaanxi Province(2024JC-YBMS-123); Service Local Projects in Shaanxi Provincial Education Department(23JC001)

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Abstract

The fluorescent probe TPE-Py was designed and synthesized, and its structure was confirmed by NMR and HRMS. The recognition properties of probe TPE-Py for metal ions have been studied through fluorescence spectrophotometry and cell imaging experiments in HeLa cells. The results showed that TPE-Py had good selectivity and sensitivity for Cu^2＋. Among various metal ions, TPE-Py only showed exclusive fluorescence turn-off sensing on Cu^2＋ in H₂O/THF (V∶V=9∶1). The results of cell imaging experiments showed that the probe TPE-Py could detect Cu^2＋ in lipid droplets of cells.

Key words: aggregation-induced emission, fluorescent sensor, ion recognition, cell imaging

Cite this article

Xiaolong Su, Jianpeng Li, Mengxin Liu, Li Zou, Desuo Yang, Haitao Feng. Synthesis of Tetraphenylethylene Based Amides for Detection of Copper(II) Ion with High Sensitivity and Selectivity[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2581-2587.

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Fig. & Tab. 8

Figure 1. (A) Fluorescence spectra of TPE-Py (10 μmo/L) in THF/H2O mixture with different H2O fractions, and (B) relative fluorescence intensity in different THF/H2O mixtures at 480 nm (λex=330 nm)

Figure 2. (A) Selectivity of probe TPE-Py for different metal ions (10 μmol/L), (B) interference study of probe TPE-Py-Cu2＋ (λex=330 nm, c=10 μmol/L), and (C) fluorescent photos of probe TPE-Py (10 μmol/L) after addition 1 equiv. of different metal ion

Figure 3. (A) Fluorescence spectrum change of TPE-Py with Cu2＋ in H2O/THF (V∶V=9∶1), and (B) linear relationship between fluorescence intensity of TPE-Py and Cu2＋ concentration at 480 nm

Figure 4. (A) Job plot of probe TPE-Py and Cu2＋, and (B) possible coordination modes between TPE-Py and Cu2＋

Figure 5. SEM images of (A, C) TPE-Py and (B, D) TPE-Py＋Cu2＋ in H2O/THF (V∶V=9∶1)

Figure 6. Viability of HeLa cells treated with different concentrations of TPE-Py

Figure 7. (A) Fluorescence image of HeLa cells with 10 μmol/L TPE-Py-NPs, and (B) fluorescence image of HeLa cells with 10 μmol/L TPE-Py-NPs＋10 μmol/L Cu2＋ Bright field transmission images (A1, B1), fluorescence dark field transmission images (A2, B2), and superimposed field transmission images (A3, B3).

Figure 8. (A) Crystal structure diagram of probe TPE-Py, and (B) π-π stacking in probe TPE-Py and hydrogen bonding with solvent molecules

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四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu^2＋

Synthesis of Tetraphenylethylene Based Amides for Detection of Copper(II) Ion with High Sensitivity and Selectivity

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References 27

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四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu2＋

Synthesis of Tetraphenylethylene Based Amides for Detection of Copper(II) Ion with High Sensitivity and Selectivity

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PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 8

References 27

Related Articles 15

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四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu^2＋