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)

文章分享

1. 326.pdf(1178KB)

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

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.

参考文献 27

[1]	Maret, W. Adv. Nutr. 2013, 4, 82. doi: 10.3945/an.112.003038
[2]	Xu, H.; Zhu, C.; Chen, Y.; Bai, Y.; Han, Z.; Yao, S.; Jiao, Y.; Yuan, H.; He, W.; Guo, Z. Chem. Sci. 2020, 11, 11037. doi: 10.1039/D0SC03037F
[3]	Plum, L. M.; Rink, L.; Haase H. Int. J. Environ. Res. Public Health 2010, 7, 1342. doi: 10.3390/ijerph7041342
[4]	Merriman, C.; Huang, Q.; Rutter, G. A.; Fu, D. J. Biol. Chem. 2016, 29, 26950.
[5]	Carter, K. P.; Young, A. M.; Palmer, A. E. Chem. Rev. 2014, 114, 4564. doi: 10.1021/cr400546e pmid: 24588137
[6]	Zhang, J.; Yan, Z.; Wang, S.; She, M.; Zhang, Z.; Cai, W.; Liu, P.; Li, J. Dyes Pigm. 2018, 150, 112. doi: 10.1016/j.dyepig.2017.11.012
[7]	Zhang, J.; Zhan, Y.; Qi, Y.; Wang, R.; Meng, L. Chin. J. Org. Chem. 2020, 40, 1847. (in Chinese) doi: 10.6023/cjoc202002025
	(张继东, 詹妍, 齐怡, 王瑞鹏, 孟莉, 有机化学, 2020, 40, 1847.) doi: 10.6023/cjoc202002025
[8]	Wu, D.; Sedgwick, A. C.; Gunnlaugsson, T.; Akkaya, E. U.; Yoon, J.; James, T. D. Chem. Soc. Rev. 2017, 46, 710.
[9]	Nie, J.; Li, N.; Ni, Z.; Zhao, Y.; Zhang, L. Tetrahedron Lett. 2017, 58, 1980. doi: 10.1016/j.tetlet.2017.04.027
[10]	Pan, S.; Tang, H.; Song, Z.; Li, J.; Guo, Y. Chin. J. Chem. 2017, 35, 1263. doi: 10.1002/cjoc.201600923
[11]	Cao, J., Zhao, C.; Wang, X.; Zhang, Y.; Zhu, W. Chem. Commun. 2012, 48, 9897. doi: 10.1039/c2cc35080g
[12]	Rai, A.; Singh, A. K.; Sonkar, A. K.; Tripathi, K.; Mishra, L. Spectrochim. Acta, Part A 2019, 216, 1. doi: 10.1016/j.saa.2019.03.003
[13]	Burdette, S. C.; Walkup, G. K.; Spingler, B.; Tsien, R. Y.; Lippard, S. J. J. Am. Chem. Soc. 2001, 123, 7831. doi: 10.1021/ja010059l pmid: 11493056
[14]	Luo, J.; Xie, Z.; Lam, J. W.; Cheng, L.; Chen, H.; Qiu, C.; Tang, B. Z. Chem. Commun. 2001, 18, 1740.
[15]	Tang, A.; Yin, Y.; Chen, Z.; Fan, C.; Liu, G.; Pu, S. Tetrahedron 2019, 75, 130489. doi: 10.1016/j.tet.2019.130489
[16]	He, X.; Wang, X.; Zhang, L.; Fang, G.; Liu, J.; Wang, S. Sens. Actuators, B Chem. 2018, 271, 289. doi: 10.1016/j.snb.2018.05.082
[17]	Sun, H.; Jiang, Y.; Nie, J.; Wei, J.; Miao, B.; Zhao, Y.; Ni, Z. Mater. Chem. Front. 2021, 5, 347. doi: 10.1039/D0QM00623H
[18]	Jiang, S.; Chen, S.; Wang, Z.; Guo, H.; Yang, F. Sens. Actuators, B Chem. 2020, 308, 127734. doi: 10.1016/j.snb.2020.127734
[19]	Li, Z.; Huo, Y.; Yang, X.; Ji, S. Chin. J. Org. Chem. 2016, 36, 2317. (in Chinese) doi: 10.6023/cjoc201604023
	(李宗植, 霍延平, 阳香华, 籍少敏, 有机化学, 2016, 36, 2317.) doi: 10.6023/cjoc201604023
[20]	Zhou, Z.; Yan, X.; Saha, M. L.; Zhang, M.; Wang, M.; Li, X.; Stang, P. J. J. Am. Chem. Soc. 2016, 138, 13131. doi: 10.1021/jacs.6b07173
[21]	Yan, X.; Wang, H.; Hauke, C. E.; Cook, T. R.; Wang, M.; Saha, M. L.; Stang, P. J. J. Am. Chem. Soc. 2015, 137, 15276. doi: 10.1021/jacs.5b10130
[22]	Hong, Y.; Chen, S.; Leung, C. W. T.; Lam, J. W. Y.; Liu, J.; Tseng, N. W.; Tang, B. Z. ACS Appl. Mater. Interfaces 2011, 3, 3411. doi: 10.1021/am2009162
[23]	Yang, Y.; Gao, C. Y.; Zhang, N.; Dong, D. Sens. Actuators, B Chem. 2016, 222, 741. doi: 10.1016/j.snb.2015.08.125
[24]	Mu, C.; Zhang, Z.; Hou, Y.; Liu, H.; Ma, L.; Li, X.; Zhang, M. Angew. Chem., Int. Ed. 2021, 133, 12401. doi: 10.1002/ange.202100463
[25]	Wang, L.; Li, Y.; You, X.; Xu, K.; Feng, Q.; Wang, J., Hou, H.; Liu, Y.; Li, K. J. Mater. Chem. C 2017, 5, 65. doi: 10.1039/C6TC03791G
[26]	Jia, J.; Zhao H. Org. Electron. 2019, 73, 55. doi: 10.1016/j.orgel.2019.05.050
[27]	Sedgwick, A. C.; Wu, L.; Han, H. H.; Bull, S. D.; He, X. P.; James, T. D.; Yoon, J.; Sessler, J. L.; Tang, B.Z.; Tian, H. Chem. Soc. Rev. 2018, 47, 8842. doi: 10.1039/c8cs00185e pmid: 30361725

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

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 10

参考文献 27

相关文章 15

编辑推荐 0

相关统计

本文评价

[1]	张莹珍, 江丹丹, 李娟华, 王菁菁, 刘昆明, 刘晋彪. 高选择性硒代半胱氨酸荧光探针的构建策略及成像[J]. 有机化学, 2024, 44(1): 41-53.
[2]	杨维清, 葛宴兵, 陈元元, 刘萍, 付海燕, 马梦林. 1,8-萘酰亚胺衍生物的设计、合成及其对半胱氨酸的识别研究[J]. 有机化学, 2024, 44(1): 180-194.
[3]	章炜, 夏欢, 曹昕, 徐彬瑜, 李峥沄. 柔性锌离子电池水凝胶电解质研究进展[J]. 有机化学, 2024, 44(1): 148-158.
[4]	李焕清, 陈兆华, 陈祖佳, 邱琪雯, 张又才, 陈思鸿, 汪朝阳. 基于有机小分子的汞离子荧光探针研究进展[J]. 有机化学, 2023, 43(9): 3067-3077.
[5]	丁炳辉, 韩少辉, 熊海青, 王本花, 左伯军, 宋相志. 高选择性比率型荧光探针用于急性肺损伤中次氯酸的检测[J]. 有机化学, 2023, 43(8): 2878-2884.
[6]	赵洋, 陈盼盼, 韩立志, 王恩举. 三苯基咪唑衍生物的聚集诱导发光性质及其细胞成像应用[J]. 有机化学, 2023, 43(7): 2454-2461.
[7]	刘铃, 浩涛涛, 伍晚花, 杨成. 利用超分子策略构筑具有聚集诱导发光(AIE)功能的二苯乙烯型分子开关[J]. 有机化学, 2023, 43(6): 2189-2196.
[8]	刘甜甜, 张鸿鹏, 焦晓梦, 白银娟. 多信号同时检测生物硫醇荧光探针的研究进展[J]. 有机化学, 2023, 43(6): 2081-2095.
[9]	李宜芳, 王耀, 牛华伟, 陈秀金, 李兆周, 王永国. 线粒体靶向的二氧化硫荧光探针研究进展[J]. 有机化学, 2023, 43(6): 1952-1962.
[10]	刘飞冉, 敬静, 张小玲. 细胞器靶向型半胱氨酸荧光探针研究进展[J]. 有机化学, 2023, 43(6): 2053-2067.
[11]	陈志华, 胡艳, 马丽丽, 张子怡, 刘传祥. 基于氢化吡啶辅助氨基氧化策略的次氯酸根荧光探针的设计、合成及其性能研究[J]. 有机化学, 2023, 43(2): 718-724.
[12]	唐宏伟, 王超, 钟克利, 侯淑华, 汤立军, 边延江. 一种裸眼和荧光双通道快速检测Hg²⁺的探针及其多种应用[J]. 有机化学, 2023, 43(2): 712-717.
[13]	周五, 彭敏, 梁庆祥, 吴爱斌, 舒文明, 余维初. 高选择和高灵敏检测溶液和气相中硫化氢的新型萘酰亚胺类开启型荧光探针[J]. 有机化学, 2023, 43(12): 4277-4283.
[14]	张越华, 聂飞, 周路, 王晓烽, 刘源, 霍延平, 陈文铖, 赵祖金. 苯并噻唑酮类热活化延迟荧光材料的合成及其光电性能研究[J]. 有机化学, 2023, 43(11): 3876-3887.
[15]	余富欢, 周志宽, 谢威, 周传庭, 盖立志, 卢华. 硅烷桥联四苯乙烯-寡聚噻吩衍生物的结构与光谱性质[J]. 有机化学, 2023, 43(10): 3652-3660.