Citation: Li Yingjun, Zhang Nan, Liu Jihong, Jin Kun, Wang Siyuan. Detection of HSO₄^- Ion with a Colorimetric and Fluorescent Probe Based on Hydrolysis Reaction of Carbazole-Derived Schiff Base in Aqueous Medium[J]. Chinese Journal of Organic Chemistry, ;2018, 38(11): 3026-3031. doi: 10.6023/cjoc201804041 shu

Detection of HSO₄^- Ion with a Colorimetric and Fluorescent Probe Based on Hydrolysis Reaction of Carbazole-Derived Schiff Base in Aqueous Medium

Li Yingjun ^a,, ,
Zhang Nan ^a ,
Liu Jihong ^b ,
Jin Kun ^c ,
Wang Siyuan ^a

a.
College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029
b.
Chemistry Analysis & Research Center, Faculty of Chemical, Environmental & Biological Science and Technology, Dalian University of Technology, Dalian 116023
c.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012

Corresponding author: Li Yingjun, chemlab.lnnu@163.com
Received Date: 22 April 2018
Revised Date: 22 June 2018
Available Online: 16 November 2018
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 carbazole-based Schiff base derivative L was synthesized and evaluated for the property of selective detection of HSO₄^- ion in aqueous medium. N-(9-Ethyl-carbazol-3-yl)-1-methyl-1-(4-nitrophenyl)-methanimine (L) selectively recognized HSO₄^- ion in CH₃CN-H₂O (V:V=9:1) via the hydrolysis reaction of Schiff bases to elicit a distinct visual colour change from orange to colorless with a significant blue fluorescence under the UV lamp. The fluorescence enhancement phenomenon caused by HSO₄^- ion did not change in the presence of other anions. The sensing mechanism of probe L for HSO₄^- had been investigated by Job's plot, ¹H NMR titration spectra and HRMS spectrum. The detection limit for the HSO₄^- ion was determined as 1.91×10^-8mol·L^-1. The compound L can be used as a highly selective and sensitive colorimetric, and fluorescent turn-on probe for HSO₄^-.
- HSO₄^-,
- carbazole,
- Schiff base,
- colorimetric,
- fluorescent,
- hydrolysis
1. [1]
  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
2. [2]
  Long, Y.; Zhou, J.; Yang, M. P.; Liu, X. J.; Zhang, M.; Yang, B. Q. Sens. Actuators, B:Chem. 2016, 232, 327. doi: 10.1016/j.snb.2016.03.157
3. [3]
  Wang, L. Y.; Ou, J. J.; Fang, G. P.; Cao, D. R. Sens. Actuators, B:Chem. 2016, 222, 1184. doi: 10.1016/j.snb.2015.08.008
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:Chem. 2014, 190, 792. doi: 10.1016/j.snb.2013.09.045
5. [5]
  Wei, T. B.; Li, W. T.; Li, Q.; Qu, W. J.; Li, H.; Yan, G. T.; Lin, Q.; Yao, H.; Zhang, Y. M. RSC Adv. 2016, 6, 43832. doi: 10.1039/C6RA06769G
6. [6]
  Cheng, X. H.; Zhong, Z. C.; Ye, T. T.; Zhang, B. J. Chin. J. Org. Chem. 2016, 36, 2822(in Chinese).
7. [7]
  Chen, X. X.; Leng, T. H.; Wang, C. Y.; Shen, Y. J.; Zhu, W. H. Dyes Pigm. 2017, 141, 299. doi: 10.1016/j.dyepig.2017.02.008
8. [8]
  Suganya, S.; Velmathi, S. Sens. Actuators, B:Chem. 2015, 221, 1104.
9. [9]
  Singh, A.; Sahoo, S. K.; Trivedi, D. R. Spectrochim. Acta, Part A 2018, 188, 596.
10. [10]
  Ashton, T. D.; Jolliffe, K. A.; Pfeffer, F. M. Chem. Soc. Rev. 2015, 44, 4547. doi: 10.1039/C4CS00372A
11. [11]
  Upadhyay, Y.; Bothra, S.; Kumar, R.; Choi, H. J.; Sahoo, S. K. Spectrochim. Acta, Part A 2017, 180, 44. doi: 10.1016/j.saa.2017.02.057
12. [12]
  Anand, T.; Sivaramana, G.; Iniya, M.; Siva, A.; Chellappa, D. Anal. Chim. Acta 2015, 876, 1. doi: 10.1016/j.aca.2015.03.035
13. [13]
  Qu, W. J.; Wei, T. B.; Lin, Q.; Li, W. T.; Su, J. X.; Liang, G. Y.; Zhang, Y. M. Sens. Actuators, B:Chem. 2016, 232, 115. doi: 10.1016/j.snb.2016.03.120
14. [14]
  Lohar, S.; Sinha, S.; Ghosh, S.; Das, D. Spectrochim. Acta, Part A 2016, 155, 75. doi: 10.1016/j.saa.2015.10.018
15. [15]
  Wang, L. Y.; Yang, L. L.; Cao, D. R. J. Fluoresc. 2014, 24, 1347. doi: 10.1007/s10895-014-1421-0
16. [16]
  Goswami, S.; Das, S.; Aich, K.; Sarkar, D.; Mondal, T. K. Tetrahedron Lett. 2013, 54, 6892. doi: 10.1016/j.tetlet.2013.10.033
17. [17]
  Kim, H. J.; Bhuniya, S.; Mahajan, R. K.; Puri, R.; Liu, H. G.; Ko, K. C.; Lee, J. Y.; Kim, J. S. Chem. Commun. 2009, 7128.
18. [18]
  Li, P.; Zhang, Y. M.; Lin, Q.; Li, J. Q.; Wei, T. B. Spectrochim. Acta, Part A 2012, 90, 152. doi: 10.1016/j.saa.2012.01.026
19. [19]
  Fegade, U.; Sharma, H.; Tayade, K.; Attarde, S.; Singh, N.; Kuwar, A. Org. Biomol. Chem. 2013, 11, 6824. doi: 10.1039/c3ob41291a
20. [20]
  Sain, D.; Kumari, C.; Kumar, A.; Dey, S. Sens. Actuators, B:Chem. 2015, 221, 849. doi: 10.1016/j.snb.2015.07.029
21. [21]
  Goel, R.; Sharma, S.; Paul, K.; Luxami, V. Sens. Actuators, B:Chem. 2017, 246, 776. doi: 10.1016/j.snb.2017.02.090
22. [22]
  Xue, W. J.; Li, L.; Li, Q.; Wu, A. X. Talanta 2012, 88, 734. doi: 10.1016/j.talanta.2011.11.033
23. [23]
  Sen, B.; Mukherjee, M.; Pal, S.; Sen, S.; Chattopadhyay, P. RSC Adv. 2015, 5, 50532. doi: 10.1039/C5RA09121G
24. [24]
  Kaur, P.; Kaur, H.; Singh, K. Analyst 2013, 138, 425. doi: 10.1039/C2AN36100K
25. [25]
  Wei, T. B.; Li, W. T.; Li, Q.; Qu, W. J.; Li, H.; Yan, G. T.; Lin, Q.; Yao, H.; Zhang, Y. M. RSC Adv. 2016, 6, 43832. doi: 10.1039/C6RA06769G
26. [26]
  Fegade, U.; Sahoo, S. K.; Singh, A.; Mahulikar, P.; Attarde, S.; Singh, N.; Kuwar, A. RSC Adv. 2014, 4, 15288. doi: 10.1039/c3ra47935h
27. [27]
  Kumar, V.; Kumar, A.; Diwan, U.; Upadhyay, K. K. Chem. Commun. 2012, 48, 9540. doi: 10.1039/c2cc33130f
28. [28]
  Lin, C. Y.; Huang, K. F.; Yen, Y. P. J. Spectrochim. Acta, Part A 2013, 115, 552. doi: 10.1016/j.saa.2013.06.083
29. [29]
  Erdemir, S.; Tabakci, B.; Tabakci, M. Sens. Actuators, B:Chem. 2016, 228, 109. doi: 10.1016/j.snb.2016.01.017
30. [30]
  Arshad, M.; Jadoon, M.; Iqbal, Z.; Fatima, M.; Ali, M.; Ayub, K.; Qureshic, A. M.; Ashraf, M.; Arshad, M. N.; Asiri, A. M.; Waseem, A.; Mahmood, T. J. Mol. Struct. 2017, 1133, 80. doi: 10.1016/j.molstruc.2016.11.065
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Detection of HSO4- Ion with a Colorimetric and Fluorescent Probe Based on Hydrolysis Reaction of Carbazole-Derived Schiff Base in Aqueous Medium

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通讯作者: 陈斌, bchen63@163.com

Detection of HSO₄^- Ion with a Colorimetric and Fluorescent Probe Based on Hydrolysis Reaction of Carbazole-Derived Schiff Base in Aqueous Medium