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

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Chemistry of Heterocyclic Compounds Aims and scope

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+.

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References

  1. Carter, K. P.; Young, A. M.; Palmer, A. E. Chem. Rev. 2014, 114, 4564.

    Article  CAS  Google Scholar 

  2. Li, H.; Fan, J.; Peng, X. Chem. Soc. Rev. 2013, 42, 7943.

    Article  CAS  Google Scholar 

  3. Dai, H. L.; Yan, Y. Y.; Guo, Y.; Fan, L. L.; Che, Z. P.; Xu, H. Chem.–Eur. J. 2012, 18, 11188.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

  7. Burdo, J. R.; Connor, J. R. BioMetals 2003, 16, 63.

    Article  CAS  Google Scholar 

  8. Minkin, V. I.; Bren', V. A.; Dubonosov, V. A.; Tsukanov, A. V. Chem. Heterocycl. Compd. 2012, 48, 107. [Khim. Geterotsikl. Soedin. 2012, 112.]

  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.

    Article  CAS  Google Scholar 

  10. Wu, H.-L.; Aderinto, S. O.; Xu, Y.-L.; Zhang, H.; Fan, X.-Y. J. Appl. Spectrosc. 2017, 84, 25.

    Article  CAS  Google Scholar 

  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.]

  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.]

  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.

    Article  CAS  Google Scholar 

  14. Chai, M. M.; Li, M.; Zhang, D.; Wang, C.-C.; Ye, Y.; Zhao, Y. F. Luminescence 2013, 28, 557.

    Article  CAS  Google Scholar 

  15. Zhang, Y. Q.; Wang, G.; Zhang, J. P. Sens. Actuators, B 2014, 200, 259.

    Article  CAS  Google Scholar 

  16. Zhao, B.; Liu, T.; Fang, Y.; Wang, L.Y.; Kan, W.; Deng, Q. G.; Song, B. Sens. Actuators, B 2017, 246, 370.

    Article  CAS  Google Scholar 

  17. Tang, L. J.; Wu, D.; Hou, S. H.; Wen, X.; Dai, X. Bull. Korean Chem. Soc. 2014, 35, 2326.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  20. Gündüz, Z. Y.; Gündüz, C.; Özpinar, C.; Urucu, O. A. Spectrochim. Acta, Part A 2015, 136, 1679.

    Article  Google Scholar 

  21. Cao, B.-N.; Hu, Q.; Huang, Y.; Jia, C.-M.; Zhang, Q. Chem. Res. Chin. Univ. 2013, 29, 419.

    Article  CAS  Google Scholar 

  22. Mergu, N.; Gupta, V. K. Sens. Actuators, B 2014, 210, 408.

  23. Vikneswaran, R.; Syafiq, M. S.; Eltayeb, N. E.; Kamaruddin, M. N.; Ramesh, S.; Yahya, R. Spectrochim. Acta, Part A 2015, 150, 175.

  24. Yang, L. L.; Zhu, W. J.; Fang, M.; Zhang, Q.; Li, C. Spectrochim. Acta, Part A 2013, 109, 186.

  25. Zakrzewska, A.; Zalesny, R.; Kolehmainen, E.; Osmia1owski, B.; Jedrzejewska, B.; Agren, H.; Pietrzak, M. Dyes Pigm. 2013, 99, 957.

    Article  CAS  Google Scholar 

  26. Osmialowski, B.; Zakrzewska, A.; Jedrzejewska, B.; Grabarz, A.; Zalesny, R.; Bartkowiak, W.; Kolehmainen, E. J. Org. Chem. 2015, 80, 2072.

    Article  CAS  Google Scholar 

  27. Zhao, B.; Liu, T.; Fang, Y.; Wang, L. Y.; Kan, W.; Deng, Q. G.; Song, B. Sens. Actuators, B 2017, 246, 370.

    Article  CAS  Google Scholar 

  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.

    Article  Google Scholar 

  29. Ghosh, K.; Rathi, S.; Rathi, P.; Gupta, P.; Vashisth, P.; Pruthi, V. Eur. J. Inorg. Chem. 2015, 311.

  30. Goswami, S.; Das, S.; Aich, K. Tetrahedron Lett. 2013, 54, 4620.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  32. Hibbert, D. B.; Thordarson, P. Chem. Commun. 2016, 52, 12792.

    Article  Google Scholar 

  33. Liu, S.-R.; Wu, S.-P. J. Fluoresc. 2011, 21, 1599.

    Article  CAS  Google Scholar 

  34. Yi, C.; Tian, W.; Song, B.; Zheng, Y.; Qi, Z.; Qi, Q.; Sun, Y. J. Lumin. 2013, 141, 15.

    Article  CAS  Google Scholar 

  35. Yin, J.; Bing, Q. J.; Wang, L.; Wang, G. Spectrochim. Acta, Part A 2018, 189, 495.

  36. Chen, H. L.; Bao, X. F.; Shu, H.; Zhou, B. J.; Ye, R. L.; Zhu, J. Sens. Actuators, B 2017, 242, 921.

    Article  CAS  Google Scholar 

  37. Liu, J. W.; Lu, Y. J. Am. Chem. Soc. 2007, 129, 9838.

    Article  CAS  Google Scholar 

  38. Hwang, S.-H.; Wang, P.; Moorefield, C. N.; Godinez, L. A.; Manriquez, J.; Bustos, E.; Newkome, G. R. Chem. Commun. 2005, 4672.

  39. Grigoras, M.; Antonoaia, N.-C. Eur. Polym. J. 2005, 41, 1079.

    Article  CAS  Google Scholar 

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Acknowledgements

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

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Correspondence to Yi He.

Additional information

Supplementary information file containing 1H and 13C NMR, MS, emission, fluorescence and spectrophotometric titration spectra of compound 1 is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(2), 146–152

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He, Y., Yin, J. & Wang, G. New selective “on-off” fluorescence chemosensor based on carbazole Schiff base for Fe3+ detection. Chem Heterocycl Comp 54, 146–152 (2018). https://doi.org/10.1007/s10593-018-2246-6

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  • DOI: https://doi.org/10.1007/s10593-018-2246-6

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