Citation: Zhu Wenbin, Lü Xiaolan, Zhu Jianghua, Cao Qianyong. Norbornene-Based Triazoles for Fluorescent Sensing of Metal Ions[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 624-629. doi: 10.6023/cjoc201611004 shu

Norbornene-Based Triazoles for Fluorescent Sensing of Metal Ions

Department of Chemistry, Nanchang University, Nanchang 330031

Corresponding author: Cao Qianyong, cqyong@ncu.edu.cn
Received Date: 2 November 2016
Revised Date: 12 December 2016

Fund Project: Project supported by the National Natural Science Foundation of China 21462027

Figures(8)

A new macrocyclic norbornene-based bis-triazole (1) containing anthracene fluorophore and its acyclic analog 2 have been designed and synthesized by "click reaction", and their fluorescence recognition abilities towards various metal ions have been investigated. In CH₃CN-H₂O (V:V=90:10) solution, cyclic receptor 1 shows excusive turn-off fluorescent sensing of Zn²⁺. However, acyclic receptor 2 exhibits fluorescence changes towards Zn²⁺, Hg²⁺ and Cu²⁺. Upon addition Zn²⁺, the fluorescence of 2 give a large enhancement, while the addition of Hg²⁺ and Cu²⁺ leads a fluorescence quenching effect. In addition, the binding mechanisms between receptors and metal ions have been discussed via ¹H NMR titration and density functional theory (DFT) calculation technique.
- norbornene,
- anthracene,
- triazole,
- fluorescence,
- metal ions recognition
1. [1]
  Masayuki, M.; Michael, M.; Peter, W.; Richard, A.; Kim, D. Org. Lett. 2005, 7, 4943. doi: 10.1021/ol051919w
2. [2]
  Kallol, B.; Anand, K.; Moupriya, N.; Soumen, B. Anal. Chem. 2014, 86, 2740. doi: 10.1021/ac404160v
3. [3]
  Zhang, X.; Guo, C.; Li, Z.; Shen, G.; Yu, R. Anal. Chem. 2002, 74, 821. doi: 10.1021/ac0109218
4. [4]
  Seraphine, V.; Hasan, A.; Murat, S.; Jun, Y.; Chuan, H. J. Am. Chem. Soc. 2010, 132, 2567 doi: 10.1021/ja9097324
5. [5]
  Wu, L.; Guo, Q.; Liu, Y.; Sun, Q. Anal. Chem. 2015, 87, 5318. doi: 10.1021/acs.analchem.5b00514
6. [6]
  Koushik, G.; Sudipto, D.; Shibashis, H.; Aradhita, B.; Corrado, R.; Partha, R. J. Mol. Struct. 2016, 325, 1118.
7. [7]
  Mehdi, A.; Roghayeh, S.; Soraia, M. Sens. Actuators, B 2016, 233, 355. doi: 10.1016/j.snb.2016.04.077
8. [8]
  Ding, Y.; Zhu, W.-H.; Xie, Y. Chem. Rev. 2017, 117, 2203. doi: 10.1021/acs.chemrev.6b00021
9. [9]
  Ding, Y.; Li, X.; Li, T.; Zhu, W.; Xie, Y. J. Org. Chem. 2013, 78, 5328. doi: 10.1021/jo400454e
10. [10]
  Xie, Y.; Wei, P.; Li, X.; Hong, T.; Zhang, K.; Furuta, H. J. Am. Chem. Soc. 2013, 135, 19119. doi: 10.1021/ja4112644
11. [11]
  Ding, Y.; Tang, Y.; Zhu, W.; Xie, Y. Chem. Soc. Rev. 2015, 44, 1101. doi: 10.1039/C4CS00436A
12. [12]
  Tang, Y.; Ding, Y.; Li, X.; Ågren, H.; Li, T.; Zhang, W.; Xie, Y. Sen. Actuators, B 2015, 206, 291. doi: 10.1016/j.snb.2014.09.060
13. [13]
  Martınez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419. doi: 10.1021/cr010421e
14. [14]
  Kolb, H.; Finn, M.; Sharpless, B. Angew. Chem., Int. Ed. 2001, 40, 2004. doi: 10.1002/(ISSN)1521-3773
15. [15]
  Lau, Y. H.; Rutledge, P. J.; Watkinson, M.; Todd, M. H. Chem. Soc. Rev. 2011, 40, 2848. doi: 10.1039/c0cs00143k
16. [16]
  Ge, J.; Liu, Z.; Cao, Q.; Chen, Y; Zhu, J. Chem. Asian J. 2016, 11, 687. doi: 10.1002/asia.v11.5
17. [17]
  Dai, B.; Cao, Q.; Wang, L.; Wang, Z.; Yang, Z. Inorg. Chim. Acta 2014, 423, 163. doi: 10.1016/j.ica.2014.08.015
18. [18]
  Zhu, J.; Fan, X.; Cao, Q. Inorg. Chim. Acta 2016, 451, 111. doi: 10.1016/j.ica.2016.07.021
19. [19]
  Wang, Z; Palacios, M.; Pavel, A. Anal. Chem. 2008, 80, 7451. doi: 10.1021/ac801165v
20. [20]
  Wu, Y.; Tan, Y.; Wu, J.; Chen, S.; Chen, Y.; Zhou, X.; Jiang, Y.; Tan, C. ACS Appl. Mater. Interfaces 2015, 7, 6882. doi: 10.1021/acsami.5b00587
21. [21]
  Wang, Z.; Dai, B.; Qiu, J.; Cao, Q.; Ge, J. Chin. J. Org. Chem. 2015, 35, 2383 (in Chinese). doi: 10.6023/cjoc201506021
22. [22]
  Emiliano, T.; Arna, K.; Lisa, M.; Matthew H. T.; Michael, W. Inorg. Chem. 2009, 48, 319. doi: 10.1021/ic8017634
23. [23]
  Sui, B.; Kim, B.; Zhang, Y.; Frazer, A.; Belfield, K. ACS Appl. Mater. Inter. 2013, 5, 2920. doi: 10.1021/am400588w
24. [24]
  Maity, D.; Govindaraju, T. Inorg. Chem. 2010, 49, 7229. doi: 10.1021/ic1009994
25. [25]
  Xu, K.; Chen, Z.; Zhou, L.; Zheng, O.; Wu, X.; Guo, L.; Qiu, B.; Lin, Z.; Chen, G. Anal. Chem. 2015, 87, 816. doi: 10.1021/ac503958r
26. [26]
  Banti, D.; North, M. Tetrahedron Lett. 2002, 43, 1561. doi: 10.1016/S0040-4039(02)00009-6
27. [27]
  Zhou, L.; Sun, Q. Chem. Commun. 2015, 51, 16767. doi: 10.1039/C5CC07306E
28. [28]
  Reuter, R.; Wegner, H. Chem. Commun. 2013, 49, 146. doi: 10.1039/C2CC35974J
29. [29]
  Kumari, A.; Swamy, K. J. Org. Chem. 2016, 81, 1425. doi: 10.1021/acs.joc.5b02567
30. [30]
  Caricato, M.; Olmo, A.; Gargiulli, C.; Gattuso, G.; Pasini, D. Tetrahedron 2012, 68, 7861. doi: 10.1016/j.tet.2012.07.038
31. [31]
  Szejtli, J. Cyclodextrine Technology, Kluwer Academic Publishers, Dodrecht, The Netherlands, 1988.
32. [32]
  Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39, 1262. doi: 10.1039/b818033b
1. [1]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
2. [2]
  Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
3. [3]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
4. [4]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
5. [5]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
6. [6]
  Zehua Zhang , Haitao Yu , Yanyu Qi . 多重共振TADF分子的设计策略. Acta Physico-Chimica Sinica, 2025, 41(1): 2309042-. doi: 10.3866/PKU.WHXB202309042
7. [7]
  Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
8. [8]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
9. [9]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
10. [10]
  Jiming XI , Yukang TENG , Rui ZHANG , Zhenzhong LU . Fluorescent coordination polymers based on anthracene-and pyrene-derivative ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 847-854. doi: 10.11862/CJIC.20240367
11. [11]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
12. [12]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
13. [13]
  Mi Wen , Baoshuo Jia , Yongqi Chai , Tong Wang , Jianbo Liu , Hailong Wu . Improvement of Fluorescence Quantitative Analysis Experiment: Simultaneous Determination of Rhodamine 6G and Rhodamine 123 in Food Using Chemometrics-Assisted Three-Dimensional Fluorescence Method. University Chemistry, 2025, 40(4): 390-398. doi: 10.12461/PKU.DXHX202405147
14. [14]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
15. [15]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
16. [16]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
17. [17]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
18. [18]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
19. [19]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
20. [20]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1382)
HTML views(144)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142