Citation: Li Yingjun, Zhao Yue, Jin Kun, Liu Jihong, Zhou Xiaoxia, Yang Kaidong. A Novel Benzimidazole-Hydrazone Derivative for Colorimetric and Fluorescent Recognition of F^- and AcO^-[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1013-1022. doi: 10.6023/cjoc201809025 shu

A Novel Benzimidazole-Hydrazone Derivative for Colorimetric and Fluorescent Recognition of F^- and AcO^-

Li Yingjun ^a,, ,
Zhao Yue ^a ,
Jin Kun ^b ,
Liu Jihong ^c ,
Zhou Xiaoxia ^a ,
Yang Kaidong ^a

a.
College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029
b.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012
c.
Chemistry Analysis and Inspection Center, Dalian University of Technology, Dalian 116023

Corresponding author: Li Yingjun, chemlab.lnnu@163.com
Received Date: 20 September 2018
Revised Date: 3 December 2018
Available Online: 21 April 2019
Fund Project: Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126)the Natural Science Foundation of Liaoning Province 20102126

Figures(11)

A novel benzimidazole-hydrazone derivative, N'-(2-hydroxy-1-naphthyl)methylene-2-[2-(4-methylphenylsulfonyl-methyl)-1H-benzoimidazol-1-yl]acetohydrazide (L), was synthesized and characterized by IR, ¹H NMR, ¹³C NMR, HRMS and elemental analysis. The recognition properties of L for anions were studied by naked eye, ultraviolet-vis and fluorescence spectroscopy. The results showed that the color of the solution changes from colorless to bright yellow upon addition of F^-, AcO^- and H₂PO₄^- to the CH₃CN solution of compound L. The solution of L emitted yellow fluorescence after the addition of F^- and AcO^- under the UV lamp (λ=365 nm). It indicated that compound L can be used as a probe for the naked eye to recognize F^-, AcO^- and H₂PO₄^-. The experimental results of UV and fluorescence spectroscopy showed that the probe L can recognize F^- and AcO^- with high selectivity and sensitivity. The binding constants (K_a) of probe L to F^- and AcO^- were 4.25×10³ and 2.96×10⁴ L·mol^-1, respectively. The detection limits (DL) were 3.63×10^-7 and 8.51×10^-8 mol·L^-1, respectively. The stoichiometry of complexation between L and F^-/AcO^- was 1:1, which was supported by the Job's plot and density functional theory (DFT) calculations. The mechanism of binding of L with F^-/AcO^- was established by ¹H NMR titration. The results showed that compound L can be used as a colorimetric and fluorescent probe for detecting F^- and AcO^-.
- benzimidazole-hydrazone,
- anion,
- naked-eye recognition,
- colorimetric and fluorescent probe
1. [1]
  Mohammadi, A.; Sahragard, R.; Rassa, M. J. Photochem. Photobiol. A: Chem. 2017, 344, 114. doi: 10.1016/j.jphotochem.2017.05.010
2. [2]
  Wang, L. Y.; Tian, Y.; He, X. Y.; Zhao, B.; Ma, W. H.; Yang, J.; Song, B. J. Photochem. Photobiol. A: Chem. 2018, 358, 300. doi: 10.1016/j.jphotochem.2018.03.037
3. [3]
  Shi, B. B.; Zhang, Y. M.; Wei, T. B.; Lin, Q.; Yao, H.; Zhang, P.; You, X. M. Sens. Actuators, B 2014, 190, 555. doi: 10.1016/j.snb.2013.09.043
4. [4]
  Wang, C. C.; Feng, S.; Wu, L. Y.; Yan, S. Y.; Zhong, C.; Guo, P.; Huang, R.; Weng, X. C.; Zhou, X. Sens. Actuators, B 2014, 190, 792. doi: 10.1016/j.snb.2013.09.045
5. [5]
  Uahengo, V.; Zhang, Y.; Xiong, B.; Zhao, P. P.; Cai, P.; Rhyman, L.; Ramasam, P.; Hu, K.; Cheng, G. Z. J. Fluoresc. 2017, 27, 1. doi: 10.1007/s10895-016-1930-0
6. [6]
  Khanmohammadi, H.; Rezaeian, K. New J. Chem. 2014, 38, 5536. doi: 10.1039/C4NJ01077A
7. [7]
  Murali, M. G.; Vishnumurthy, K. A.; Seethamraju, S.; Ramamurthy, P. C. RSC Adv. 2014, 4, 20592. doi: 10.1039/C4RA01555J
8. [8]
  Pandian, T. S.; Cho, S. J.; Kang, J. J. Org. Chem. 2013, 78, 12121. doi: 10.1021/jo402103d
9. [9]
  Jeong, H. Y.; Lee, S. Y.; Kim, C. J. Fluoresc. 2017, 27, 4.
10. [10]
  Ghosh, S.; Masum, A. A.; Ganguly, A.; Islam, M. M.; Alam, M. A.; Guchhait, N. Spectrochim. Acta, Part A 2017, 178, 24. doi: 10.1016/j.saa.2017.01.044
11. [11]
  Parthiban, C.; Elango, K. P. Sens. Actuators, B 2017, 245, 321. doi: 10.1016/j.snb.2017.01.153
12. [12]
  Fu, Y.; Tang, H.; Liu, Z.; Zhang, W.-X.; Ren, J. Chin. J. Org. Chem. 2018, 38, 1806 (in Chinese).
13. [13]
  Zhang, C.-L.; Li, Y.-Z.; Li, J.-C.; Wang, J.; Wang, H.-Y.; Gong, R.-Q. Chin. J. Appl. Chem. 2018, 35, 197 (in Chinese). doi: 10.11944/j.issn.1000-0518.2018.02.170129
14. [14]
  Singh, A.; Tom, S.; Trivedi, D. R. J. Photochem. Photobiol. A: Chem. 2018, 353, 507. doi: 10.1016/j.jphotochem.2017.12.002
15. [15]
  Temirak, A.; Shaker, Y. M.; Ragab, F. A. F.; Ali, M. M.; Soliman, S. M.; Mortier, J.; Wolber, G.; Ali, H. I.; El Diwani, H. Arch. Pharm. Chem. Life Sci. 2014, 347, 291. doi: 10.1002/ardp.v347.4
16. [16]
  Onnis, V.; Demurtas M.; Deplano, A.; Balboni, G.; Baldisserotto, A.; Manfredini, T.; Pacifico, S.; Liekens, S.; Balzarini, J. Molecules 2016, 21, 579. doi: 10.3390/molecules21050579
17. [17]
  Li, Z. C.; Zhang, S. C.; Deng, L.; Hu, J.; Li, H.; Zhao, Y. G.; Luo, Y. F.; Huang, W. C. Med. Chem. Res. 2014, 23, 4050. doi: 10.1007/s00044-014-0981-5
18. [18]
  Kumar, V.; Basavarajaswamy, G.; Rai, M. V.; Poojary, B.; Pai, V. R.; N., S.; Bhat, M. Bioorg. Med. Chem. Lett. 2015, 25, 1420. doi: 10.1016/j.bmcl.2015.02.043
19. [19]
20. [20]
  Taha, M.; Ismail, N. H.; Jamil, W.; Rashwan, H.; Kashif, S. M.; Sain, A. A.; Adenan, M. I.; Anouar, E. H.; Ali, M.; Rahim, F.; Khan, K. M. Eur. J. Med. Chem. 2014, 84, 731. doi: 10.1016/j.ejmech.2014.07.078
21. [21]
  Bouhadir, K. H.; Koubeissi, A.; Mohsen, F. A.; El-Harakeh, M. D.; Cheaib, R.; Younes, J.; Azzi, G.; Eid, A. A. Bioorg. Med. Chem. Lett. 2016, 26, 1020. doi: 10.1016/j.bmcl.2015.12.042
22. [22]
  Eldehna, W. M.; Fares, M.; Abdel-Aziz, M. M.; Abdel-Aziz, H. A. Molecules 2015, 20, 8800. doi: 10.3390/molecules20058800
23. [23]
  Zou, G. G.; Liu, C. X.; Cong, C.; Fang, Z. T.; Yang, W.; Luo, X. M.; Jia, S. K.; Wu, F.; Zhao, X. Chem. Commun. 2018, 54, 13107. doi: 10.1039/C8CC08232D
24. [24]
  Hu, J. H.; Li, J. B.; Qi, J.; Sun, Y. Sens. Actuators, B 2015, 208, 581. doi: 10.1016/j.snb.2014.11.066
25. [25]
  Zhao, J. Y.; Zhao, Y. K.; Xu, S.; Luo, N.; Tang, R. Inorg. Chim. Acta 2015, 38, 105.
26. [26]
  Li, D. X.; Sun, X.; Huang, J. M.; Wang, Q.; Feng, Y.; Chen, M.; Meng, X. M.; Zhu, M. Z.; Wang, X. Dyes Pigm. 2016, 25, 185.
27. [27]
  Erdemir, S.; Malkondu, S. J. Lumin. 2015, 158, 401. doi: 10.1016/j.jlumin.2014.10.043
28. [28]
  Juliano, C.; Mattana, A.; Solinas, C. Transition Met. Chem. 2010, 35, 253. doi: 10.1007/s11243-009-9321-x
29. [29]
  Liao, Z.; Liu, Y.; Han, S. F.; Wang, D.; Zheng, J. Q.; Zheng, X. J.; Jin, L. P. Sens. Actuators, B 2017, 244, 914. doi: 10.1016/j.snb.2017.01.074
30. [30]
  Hu, J. H.; Li, J. B.; Sun, Y.; Pei, P. X.; Qi, J. RSC Adv. 2017, 7, 29697. doi: 10.1039/C7RA04462C
31. [31]
  Nakane, Y.; Takeda, T.; Hoshino, N.; Sakai, K.; Akutagawa, T. J. Mater. Chem. 2017, 5, 25.
32. [32]
  Wei, J.; Chai, Q.; He, L. H.; Bai, B. L.; Wang, H. T.; Li, M. Tetrahedron 2016, 72, 3073. doi: 10.1016/j.tet.2016.04.035
33. [33]
  Das, A. K.; Goswami, S. Sens. Actuators, B 2017, 245, 1062. doi: 10.1016/j.snb.2017.01.068
34. [34]
  Zhou, M. Q.; Eun, Y, J.; Guzei, I. A.; Weibel, D. B. ACS Med. Chem. Lett. 2013, 4, 880. doi: 10.1021/ml400234x
35. [35]
  Li, Y.-J.; Li, J.-Y.; Jin, K.; Cao, X. Chin. J. Magn. Reson. 2017, 34, 25 (in Chinese). doi: 10.11938/cjmr20170104
36. [36]
  Li, Y.-J.; Li, Y.-J.; Peng, L.-N.; Gao, L.-X.; Jin, K.; Sheng, L.; Zhang, N.; Wang, S.-Y.; Li, J. Chin. J. Org. Chem. 2017, 37, 485 (in Chinese).
37. [37]
  Liu, C. X.; Chen, Y. Q.; Wang, Y. F.; Wu, F.; Zhang, X.; Yang, W.; Wang, J. Q.; Chen, Y.; He, Z. Y.; Zou, G. G.; Wang, S. R.; Zhou, X. Nano Res. 2017, 10, 2449. doi: 10.1007/s12274-017-1445-2
38. [38]
  Liu, G.; Shao, J. J. Fluoresc. 2012, 22, 397. doi: 10.1007/s10895-011-0972-6
39. [39]
  Yu, M. M.; Xu, J.; Peng, C.; Li, Z. X.; Liu, C. X.; Wei, L. H. Tetrahedron 2016, 72, 273. doi: 10.1016/j.tet.2015.11.017
40. [40]
  Srikala, P.; Tarafder, K.; Trivedi, D. R. Spectrochim. Acta, Part A 2017, 170, 29. doi: 10.1016/j.saa.2016.07.001
41. [41]
  Liu, C. X.; Zou, G. G.; Peng, S.; Wang, Y. F.; Yang, W.; Wu, F.; Jiang, Z. R.; Zhang, X.; Zhou, X. Angew. Chem., Int. Ed. 2018, 57, 9689. doi: 10.1002/anie.v57.31
42. [42]
  Rahmani, R.; Boukabcha, N.; Chouaih, A.; Hamzaoui, F.; Goumri-Said, S. J. Mol. Struct. 2018, 1155, 484. doi: 10.1016/j.molstruc.2017.11.033
43. [43]
  Li, Y.-J.; Zhang, N.; Liu, J.-H.; Jin, K.; Wang, S.-Y. Chin. J. Org. Chem. 2018, 38, 485 (in Chinese).
1. [1]
  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
2. [2]
  Qiaojia GUO , Junkai CAI , Chunying DUAN . Effects of anions on the structural regulation of Zn-salen-modified metal-organic cage. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2203-2211. doi: 10.11862/CJIC.20240209
3. [3]
  Jiandong Liu , Xin Li , Daxiong Wu , Huaping Wang , Junda Huang , Jianmin Ma . Anion-Acceptor Electrolyte Additive Strategy for Optimizing Electrolyte Solvation Characteristics and Electrode Electrolyte Interphases for Li||NCM811 Battery. Acta Physico-Chimica Sinica, 2024, 40(6): 2306039-0. doi: 10.3866/PKU.WHXB202306039
4. [4]
  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
5. [5]
  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
6. [6]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 2406014-0. doi: 10.3866/PKU.WHXB202406014
7. [7]
  Zilin Hu , Yaoshen Niu , Xiaohui Rong , Yongsheng Hu . Suppression of Voltage Decay through Ni³⁺ Barrier in Anionic-Redox Active Cathode for Na-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(6): 2306005-0. doi: 10.3866/PKU.WHXB202306005
8. [8]
  Pingping LU , Shuguang ZHANG , Peipei ZHANG , Aiyun NI . Preparation of zinc sulfate open frameworks based probe materials and detection of Pb²⁺ and Fe³⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 959-968. doi: 10.11862/CJIC.20240411
9. [9]
  Ye Wang , Ruixiang Ge , Xiang Liu , Jing Li , Haohong Duan . An Anion Leaching Strategy towards Metal Oxyhydroxides Synthesis for Electrocatalytic Oxidation of Glycerol. Acta Physico-Chimica Sinica, 2024, 40(7): 2307019-0. doi: 10.3866/PKU.WHXB202307019
10. [10]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
11. [11]
  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
12. [12]
  Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
13. [13]
  Jingjie Tang , Luying Xie , Jiayu Liu , Shangyu Shi , Xinyu Sun , Jiayang Lin , Qikun Yang , Chuan'ang Yu , Zecheng Wang , Yingying Wang , Zengyang Xie . Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University. University Chemistry, 2024, 39(3): 316-326. doi: 10.3866/PKU.DXHX202309091
14. [14]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO₂ Methanation of Derived Ni-Al₂O₃ Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
15. [15]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
16. [16]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
17. [17]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
18. [18]
  Kexin Feng , Jie Zhang , Yujia Sun , Qiong Ai , Longchun Li . 乙酰二茂铁和二茂铁甲酰丙酮的合成、纯化及表征. University Chemistry, 2025, 40(8): 307-314. doi: 10.12461/PKU.DXHX202409045
19. [19]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
20. [20]
  Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(971)
HTML views(118)

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

A Novel Benzimidazole-Hydrazone Derivative for Colorimetric and Fluorescent Recognition of F- and AcO-

Metrics

通讯作者: 陈斌, bchen63@163.com

A Novel Benzimidazole-Hydrazone Derivative for Colorimetric and Fluorescent Recognition of F^- and AcO^-