Chemistry of Heterocyclic Compounds

, Volume 54, Issue 2, pp 146–152 | Cite as

New selective “on-off” fluorescence chemosensor based on carbazole Schiff base for Fe3+ detection

Article
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A new double Schiff base, carbazole, and diaminomaleonitrile-based chemosensor for Fe3+ with high sensitivity and selectivity was designed and synthesized. Addition of only Fe3+ ions induced the fluorescence quenching of the chemosensor in DMF solution. The chemosensor formed a 1:1 complex with Fe3+ with the high binding constant of 7.98·10–6 M–1. The chemosensor displayed low detection limit (3.75·10–8 M) and fast response time (15 s) to Fe3+.

Keywords

carbazole iron ion Schiff base fluorescence chemosensor 

Notes

Acknowledgements

This work was supported by the Research Fund for the Doctoral Program of Higher Education of China (20120043110007).

Supplementary material

10593_2018_2246_MOESM1_ESM.pdf (925 kb)
ESM 1 (PDF 924 kb)

References

  1. 1.
    Carter, K. P.; Young, A. M.; Palmer, A. E. Chem. Rev. 2014, 114, 4564.CrossRefGoogle Scholar
  2. 2.
    Li, H.; Fan, J.; Peng, X. Chem. Soc. Rev. 2013, 42, 7943.CrossRefGoogle Scholar
  3. 3.
    Dai, H. L.; Yan, Y. Y.; Guo, Y.; Fan, L. L.; Che, Z. P.; Xu, H. Chem.–Eur. J. 2012, 18, 11188.CrossRefGoogle Scholar
  4. 4.
    Georgopoulos, P. G.; Roy, A.; Yonone-Lioy, M. J.; Opiekun, R. E.; Lioy, P. J. J. J. Toxicol. Environ. Health, Part B 2001, 4, 341.CrossRefGoogle Scholar
  5. 5.
    Wang, Y.; Chang, H.-Q.; Wu, W.-N.; Zhao, X.-L.; Yang, Y.; Xu, Z.-Q.; Xu, Z.-H.; Jia, L. Sens. Actuators, B 2017, 239, 60.CrossRefGoogle Scholar
  6. 6.
    Frausto da Silva, J. J. R.; Williams, R. J. P. The Biological Chemistry of the Elements: The Inorganic Chemistry of Life; Oxford Universuty Press: New York, 1991, p. 344.Google Scholar
  7. 7.
    Burdo, J. R.; Connor, J. R. BioMetals 2003, 16, 63.CrossRefGoogle Scholar
  8. 8.
    Minkin, V. I.; Bren', V. A.; Dubonosov, V. A.; Tsukanov, A. V. Chem. Heterocycl. Compd. 2012, 48, 107. [Khim. Geterotsikl. Soedin. 2012, 112.]Google Scholar
  9. 9.
    Pan, J.-T.; Zhu, F.; Kong, L.; Yang, L.-M.; Tao, X.-T.; Tian, Y.-P.; Lu, H.-B.; Yang, J.-X. Chem. Pap. 2015, 69, 527.CrossRefGoogle Scholar
  10. 10.
    Wu, H.-L.; Aderinto, S. O.; Xu, Y.-L.; Zhang, H.; Fan, X.-Y. J. Appl. Spectrosc. 2017, 84, 25.CrossRefGoogle Scholar
  11. 11.
    Tolpygin, I. E.; Tihomirova, K. S.; Popova, O. S.; Nikolaeva, O. G.; Revinskii, Yu. V.; Dubonosov, A. D.; Bren, V. A. Chem. Heterocycl. Compd. 2014, 50, 41. [Khim. Geterotsikl. Soedin. 2014, 47.]Google Scholar
  12. 12.
    Tikhomirova, K. S.; Tolpygin, I. E.; Starikov, A. G.; Kaz'mina, M. A. Chem. Heterocycl. Compd. 2017, 53, 179. [Khim. Geterotsikl. Soedin. 2017, 53, 179.]Google Scholar
  13. 13.
    Wang, C.; Zhou, J. D.; Ran, G. X.; Li, F.; Zhong, Z.; Song, Q. J.; Dong, Q. C. J. Mater. Chem. C 2017, 5, 434.CrossRefGoogle Scholar
  14. 14.
    Chai, M. M.; Li, M.; Zhang, D.; Wang, C.-C.; Ye, Y.; Zhao, Y. F. Luminescence 2013, 28, 557.CrossRefGoogle Scholar
  15. 15.
    Zhang, Y. Q.; Wang, G.; Zhang, J. P. Sens. Actuators, B 2014, 200, 259.CrossRefGoogle Scholar
  16. 16.
    Zhao, B.; Liu, T.; Fang, Y.; Wang, L.Y.; Kan, W.; Deng, Q. G.; Song, B. Sens. Actuators, B 2017, 246, 370.CrossRefGoogle Scholar
  17. 17.
    Tang, L. J.; Wu, D.; Hou, S. H.; Wen, X.; Dai, X. Bull. Korean Chem. Soc. 2014, 35, 2326.CrossRefGoogle Scholar
  18. 18.
    Li, D. X.; Sun, X.; Huang, J. M.; Wang, Q.; Feng, Y.; Chen, M.; Meng, X.; Zhu, M.; Wang, X. Dyes. Pigm. 2016, 125, 185.CrossRefGoogle Scholar
  19. 19.
    Yang, L. L.; Wang, J. P.; Yang, L.; Zhang, C.; Zhang, R. L.; Zhang, Z. P.; Liu, B. H.; Jiang, C. L. RSC. Adv. 2016, 6, 56384.CrossRefGoogle Scholar
  20. 20.
    Gündüz, Z. Y.; Gündüz, C.; Özpinar, C.; Urucu, O. A. Spectrochim. Acta, Part A 2015, 136, 1679.CrossRefGoogle Scholar
  21. 21.
    Cao, B.-N.; Hu, Q.; Huang, Y.; Jia, C.-M.; Zhang, Q. Chem. Res. Chin. Univ. 2013, 29, 419.CrossRefGoogle Scholar
  22. 22.
    Mergu, N.; Gupta, V. K. Sens. Actuators, B 2014, 210, 408.Google Scholar
  23. 23.
    Vikneswaran, R.; Syafiq, M. S.; Eltayeb, N. E.; Kamaruddin, M. N.; Ramesh, S.; Yahya, R. Spectrochim. Acta, Part A 2015, 150, 175.Google Scholar
  24. 24.
    Yang, L. L.; Zhu, W. J.; Fang, M.; Zhang, Q.; Li, C. Spectrochim. Acta, Part A 2013, 109, 186.Google Scholar
  25. 25.
    Zakrzewska, A.; Zalesny, R.; Kolehmainen, E.; Osmia1owski, B.; Jedrzejewska, B.; Agren, H.; Pietrzak, M. Dyes Pigm. 2013, 99, 957.CrossRefGoogle Scholar
  26. 26.
    Osmialowski, B.; Zakrzewska, A.; Jedrzejewska, B.; Grabarz, A.; Zalesny, R.; Bartkowiak, W.; Kolehmainen, E. J. Org. Chem. 2015, 80, 2072.CrossRefGoogle Scholar
  27. 27.
    Zhao, B.; Liu, T.; Fang, Y.; Wang, L. Y.; Kan, W.; Deng, Q. G.; Song, B. Sens. Actuators, B 2017, 246, 370.CrossRefGoogle Scholar
  28. 28.
    Wu, J.-S.; Liu, W.-M.; Zhuang, X.-Q.; Wang, F.; Wang, P.-F.; Tao, S.-L.; Zhang, X.-H.; Wu, S.-K.; Lee, S.-T. Org. Lett. 2006, 9, 33.CrossRefGoogle Scholar
  29. 29.
    Ghosh, K.; Rathi, S.; Rathi, P.; Gupta, P.; Vashisth, P.; Pruthi, V. Eur. J. Inorg. Chem. 2015, 311.Google Scholar
  30. 30.
    Goswami, S.; Das, S.; Aich, K. Tetrahedron Lett. 2013, 54, 4620.CrossRefGoogle Scholar
  31. 31.
    Schaming, D.; Costa-Coquelard, C.; Lampre, I.; Sorgues, S.; Erard, M.; Liu, X.; Liu, J.; Sun, L.; Canny, J.; Thouvenot, R.; Ruhlmann, L. Inorg. Chim. Acta 2010, 363, 2185.CrossRefGoogle Scholar
  32. 32.
    Hibbert, D. B.; Thordarson, P. Chem. Commun. 2016, 52, 12792.CrossRefGoogle Scholar
  33. 33.
    Liu, S.-R.; Wu, S.-P. J. Fluoresc. 2011, 21, 1599.CrossRefGoogle Scholar
  34. 34.
    Yi, C.; Tian, W.; Song, B.; Zheng, Y.; Qi, Z.; Qi, Q.; Sun, Y. J. Lumin. 2013, 141, 15.CrossRefGoogle Scholar
  35. 35.
    Yin, J.; Bing, Q. J.; Wang, L.; Wang, G. Spectrochim. Acta, Part A 2018, 189, 495.Google Scholar
  36. 36.
    Chen, H. L.; Bao, X. F.; Shu, H.; Zhou, B. J.; Ye, R. L.; Zhu, J. Sens. Actuators, B 2017, 242, 921.CrossRefGoogle Scholar
  37. 37.
    Liu, J. W.; Lu, Y. J. Am. Chem. Soc. 2007, 129, 9838.CrossRefGoogle Scholar
  38. 38.
    Hwang, S.-H.; Wang, P.; Moorefield, C. N.; Godinez, L. A.; Manriquez, J.; Bustos, E.; Newkome, G. R. Chem. Commun. 2005, 4672.Google Scholar
  39. 39.
    Grigoras, M.; Antonoaia, N.-C. Eur. Polym. J. 2005, 41, 1079.CrossRefGoogle Scholar

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Authors and Affiliations

  1. 1.College of ChemistryJilin UniversityChangchunP. R. China
  2. 2.Faculty of ChemistryNortheast Normal UniversityChangchunP. R. China

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