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

doi:10.6023/cjoc202307021

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1337-1342.DOI: 10.6023/cjoc202307021 Previous Articles Next Articles

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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

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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Abstract

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

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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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Fig. & Tab. 9

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 395 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 ethanol 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: 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+

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)

Figure 6. Job plot of L and Zn2+

Figure 7. Crystal structure of the complex ZnL2

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

References 28

[1]	Kumar V.; Kumar A.; Singh K.; Avasthi K.; Kim J. J. Eur. J. Nutr. 2021, 60, 55. doi: 10.1007/s00394-020-02454-3
[2]	Choi S.; Cui C.; Luo Y.; Kim S. H.; Ko J. K.; Huo X.; Ma J.; Fu L.; Souza R. F.; Korichneva I.; Pan Z. FASEB J. 2018, 32, 404. doi: 10.1096/fsb2.v32.1
[3]	Shefner J. M.; Reaume A. G.; Flood D. G.; Scott R. W.; Kowall N. W.; Ferrante R. J.; Brown R. H. Neurology 1999, 53, 1239. pmid: 10522879
[4]	Wintergerst E. S.; Maggini S.; Hornig D. H. Ann. Nutr. Metab. 2006, 50, 85. doi: 10.1159/000090495 pmid: 16373990
[5]	Wong C. P.; Ho E. Mol. Nutr. Food Res. 2012, 56, 77. doi: 10.1002/mnfr.v56.1
[6]	Maares M.; Haase H. Arch. Biochem. Biophys. 2016, 611, 58. doi: S0003-9861(16)30074-1 pmid: 27021581
[7]	Zhang J.; Yan Z.; Wang S.; She M.; Zhang Z.; Cai W.; Li J. Dyes Pigm. 2018, 150, 112. doi: 10.1016/j.dyepig.2017.11.012
[8]	Yang Y.; Cao B.; Zhang Y.; Dong Y. Chin. J. Org. Chem, 2017, 37, 3024. (in Chinese) doi: 10.6023/cjoc201702024
	(杨云裳, 曹碧霞, 张应鹏, 董玉莹, 有机化学, 2017, 37, 3024.) doi: 10.6023/cjoc201702024
[9]	Fang L.; Trigiante G.; Crespo-Otero R.; Hawes C. S.; Philpott M. P.; Jones C. R.; Watkinson M. Chem. Sci. 2019, 10, 10881. doi: 10.1039/c9sc04300d pmid: 32190243
[10]	Luo J.; Xie Z.; Lam J. W.; Cheng L.; Chen H.; Qiu C.; Tang B. Z. Chem. Commun. 2001, 18, 1740.
[11]	Gao M.; Tang B. Z. ACS Sens. 2017, 2, 1382. doi: 10.1021/acssensors.7b00551
[12]	Ye F. Y.; Hu M.; Zheng Y. S. Coord. Chem. Rev. 2023, 493, 215.
[13]	Kang Z.; Yang J.; Jiang J.; Zhao L.; Zhang Y.; Tu Q.; Wang J.; Yuan M. S. Sens. Actuators, B 2022, 370, 132436. doi: 10.1016/j.snb.2022.132436
[14]	La D. D.; Bhosale S. V.; Jones L. A.; Bhosale S. V. ACS Appl. Mater. Interfaces 2017, 10, 12189. doi: 10.1021/acsami.7b12320
[15]	Feng H. T.; Yuan Y. X.; Xiong J. B.; Zheng Y. S.; Tang B. Z. Chem. Soc. Rev. 2018, 47, 7452. doi: 10.1039/C8CS00444G
[16]	Kumar K. S. S.; Girish Y. R.; Ashrafizadeh M.; Mirzaei S.; Rakesh K. P.; Gholami M. H.; Zabolian A.; Hushmandi K.; Orive, Gorka.; Kadumudi, F. B.; Dolatshahi-Pirouz, A.; Thakur, V. K.; Zarrabi, A.; Makvandi, P.; Rangappa, K. S. Coord. Chem. Rev. 2021, 447, 214135. doi: 10.1016/j.ccr.2021.214135
[17]	Guo Z.; Li G.; Wang H.; Zhao J.; Liu Y.; Tan H.; Li X.; Stang P. J.; Yan X. J. Am. Chem. Soc, 2021, 143, 9215. doi: 10.1021/jacs.1c04288
[18]	Mu C.; Zhang Z.; Hou Y.; Liu H.; Ma L.; Li X.; Ling S.; He G.; Zhang M. Angew. Chem. 2021, 133, 12401. doi: 10.1002/ange.v133.22
[19]	Zhang D.; Yu W.; Li S.; Xia Y.; Li X.; Li Y.; Yi T. J. Am. Chem. Soc. 2021, 143, 1313. doi: 10.1021/jacs.0c12522
[20]	Li Y.; Dong Y.; Cheng L.; Qin C.; Nian H.; Zhang H.; Yu Y.; Cao L. J. Am. Chem. Soc. 2019, 141, 8412. doi: 10.1021/jacs.9b02617
[21]	Wang P.; Miao X.; Meng Y.; Wang Q.; Wang J.; Duan H.; Li Y.; Li C.; Liu J.; Cao L. ACS Appl. Mater. Interfaces 2020, 12, 22630. doi: 10.1021/acsami.0c04917
[22]	Ahmed S.; Kumar A.; Mukherjee P. S. Chem. Mater. 2022, 34, 9656. doi: 10.1021/acs.chemmater.2c02409
[23]	Wang D.; Li S. J.; Cao W.; Wang Z.; Ma Y. ACS Omega 2022, 7, 18017. doi: 10.1021/acsomega.2c01414 pmid: 35664592
[24]	Tang A.; Yin Y.; Chen Z.; Fan C.; Liu G.; Pu S. Tetrahedron 2019, 75, 130489. doi: 10.1016/j.tet.2019.130489
[25]	Wang Y.; Liu H.; Chen Z.; Pu S. Spectrochim. Acta, Part A 2021, 245, 118928. doi: 10.1016/j.saa.2020.118928
[26]	Zhang J.; Yan W.; Hu W.; Guo D.; Zhang D.; Quan X.; Bu X. Chen S. Chin. J. Org. Chem. 2023, 43, 326. (in Chinese) doi: 10.6023/cjoc202207004
	(张继东, 颜婉琳, 胡文强, 郭典, 张大龙, 权校昕, 卜贤盼, 陈思宇, 有机化学, 2023, 43, 326.) doi: 10.6023/cjoc202207004
[27]	Sun H.; Jiang Y.; Nie J.; Wei J.; Miao B.; Zhao Y.; Zhang L.; Ni Z. Mater. Chem. Front. 2021, 5, 347. doi: 10.1039/D0QM00623H
[28]	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

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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