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+.
Similar content being viewed by others
References
Carter, K. P.; Young, A. M.; Palmer, A. E. Chem. Rev. 2014, 114, 4564.
Li, H.; Fan, J.; Peng, X. Chem. Soc. Rev. 2013, 42, 7943.
Dai, H. L.; Yan, Y. Y.; Guo, Y.; Fan, L. L.; Che, Z. P.; Xu, H. Chem.–Eur. J. 2012, 18, 11188.
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.
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.
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.
Burdo, J. R.; Connor, J. R. BioMetals 2003, 16, 63.
Minkin, V. I.; Bren', V. A.; Dubonosov, V. A.; Tsukanov, A. V. Chem. Heterocycl. Compd. 2012, 48, 107. [Khim. Geterotsikl. Soedin. 2012, 112.]
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.
Wu, H.-L.; Aderinto, S. O.; Xu, Y.-L.; Zhang, H.; Fan, X.-Y. J. Appl. Spectrosc. 2017, 84, 25.
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.]
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.]
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.
Chai, M. M.; Li, M.; Zhang, D.; Wang, C.-C.; Ye, Y.; Zhao, Y. F. Luminescence 2013, 28, 557.
Zhang, Y. Q.; Wang, G.; Zhang, J. P. Sens. Actuators, B 2014, 200, 259.
Zhao, B.; Liu, T.; Fang, Y.; Wang, L.Y.; Kan, W.; Deng, Q. G.; Song, B. Sens. Actuators, B 2017, 246, 370.
Tang, L. J.; Wu, D.; Hou, S. H.; Wen, X.; Dai, X. Bull. Korean Chem. Soc. 2014, 35, 2326.
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.
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.
Gündüz, Z. Y.; Gündüz, C.; Özpinar, C.; Urucu, O. A. Spectrochim. Acta, Part A 2015, 136, 1679.
Cao, B.-N.; Hu, Q.; Huang, Y.; Jia, C.-M.; Zhang, Q. Chem. Res. Chin. Univ. 2013, 29, 419.
Mergu, N.; Gupta, V. K. Sens. Actuators, B 2014, 210, 408.
Vikneswaran, R.; Syafiq, M. S.; Eltayeb, N. E.; Kamaruddin, M. N.; Ramesh, S.; Yahya, R. Spectrochim. Acta, Part A 2015, 150, 175.
Yang, L. L.; Zhu, W. J.; Fang, M.; Zhang, Q.; Li, C. Spectrochim. Acta, Part A 2013, 109, 186.
Zakrzewska, A.; Zalesny, R.; Kolehmainen, E.; Osmia1owski, B.; Jedrzejewska, B.; Agren, H.; Pietrzak, M. Dyes Pigm. 2013, 99, 957.
Osmialowski, B.; Zakrzewska, A.; Jedrzejewska, B.; Grabarz, A.; Zalesny, R.; Bartkowiak, W.; Kolehmainen, E. J. Org. Chem. 2015, 80, 2072.
Zhao, B.; Liu, T.; Fang, Y.; Wang, L. Y.; Kan, W.; Deng, Q. G.; Song, B. Sens. Actuators, B 2017, 246, 370.
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.
Ghosh, K.; Rathi, S.; Rathi, P.; Gupta, P.; Vashisth, P.; Pruthi, V. Eur. J. Inorg. Chem. 2015, 311.
Goswami, S.; Das, S.; Aich, K. Tetrahedron Lett. 2013, 54, 4620.
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.
Hibbert, D. B.; Thordarson, P. Chem. Commun. 2016, 52, 12792.
Liu, S.-R.; Wu, S.-P. J. Fluoresc. 2011, 21, 1599.
Yi, C.; Tian, W.; Song, B.; Zheng, Y.; Qi, Z.; Qi, Q.; Sun, Y. J. Lumin. 2013, 141, 15.
Yin, J.; Bing, Q. J.; Wang, L.; Wang, G. Spectrochim. Acta, Part A 2018, 189, 495.
Chen, H. L.; Bao, X. F.; Shu, H.; Zhou, B. J.; Ye, R. L.; Zhu, J. Sens. Actuators, B 2017, 242, 921.
Liu, J. W.; Lu, Y. J. Am. Chem. Soc. 2007, 129, 9838.
Hwang, S.-H.; Wang, P.; Moorefield, C. N.; Godinez, L. A.; Manriquez, J.; Bustos, E.; Newkome, G. R. Chem. Commun. 2005, 4672.
Grigoras, M.; Antonoaia, N.-C. Eur. Polym. J. 2005, 41, 1079.
Acknowledgements
This work was supported by the Research Fund for the Doctoral Program of Higher Education of China (20120043110007).
Author information
Authors and Affiliations
Corresponding author
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
Electronic supplementary material
ESM 1
(PDF 924 kb)
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-018-2246-6