DEVELOPMENT OF A NEW 4-AMINO-1,8-NAPHTHALIMIDE DERIVATIVE AS A FLUORESCENT PROBE FOR MONITORING THE DIVALENT COPPER ION
Abstract
This article presents the design and synthesis of a new variant of the 4-amino-1,8-naphthalimide fluorescent probe for monitoring the divalent copper ion, Cu2+ . The probe BRST, functionalized with two propionic carboxylic acid groups in its receptor moiety, demonstrated high selectivity and sensitivity for the detection of Cu2+ in competitive media of various metal ions in DMSO/HEPES buffer solution (1:1; pH 7.4), with a fluorescence quenching of 75.41%. Besides its good linearity with Cu2+ , the probe yielded commendable values of the association constant and the detection limit, 5.54´105 M-1 and 4.33´10-9 M, respectively. The quenching of the fluorescence intensity of the sensor in the presence of Cu2+ ions is attributable to the strong paramagnetic nature of the Cu2+ ion. The fluorescence “turn off” behavior of this simple and effective probe was successfully applied for the determination of Cu2+ levels in untreated water samples, with excellent recovery rates of 98-105.8%.
About the Authors
K. . Shen
School of Chemical and Biological Engineering, Lanzhou Jiaotong University
Russian Federation
Russian Federation
S. . Mao
School of Chemical and Biological Engineering, Lanzhou Jiaotong University
Russian Federation
Russian Federation
X. . Shi
School of Chemical and Biological Engineering, Lanzhou Jiaotong University
Russian Federation
Russian Federation
S. . Opeyemi Aderinto
School of Chemical and Biological Engineering, Lanzhou Jiaotong University
Russian Federation
Russian Federation
Y. . Xu
School of Chemical and Biological Engineering, Lanzhou Jiaotong University
Russian Federation
Russian Federation
H. . Wu
School of Chemical and Biological Engineering, Lanzhou Jiaotong University
Russian Federation
Russian Federation
References
1. N. Kaur, S. Kumar, Tetrahedron, 67, 9233-9264 (2011).
2. A. Caballero, R. Martínez, V. Lloveras, I. Ratera, J. Vidal-Gancedo, K. Wurst, A. Tárraga, P. Molina, J. Veciana, J. Am. Chem. Soc., 127, 15666-15667 (2005).
3. V. B. Bojinov, N. I. Georgiev, P. S. Nikolov, J. Photochem. Photobiol. A, 193, 129-138 (2008).
4. W. K. Dong, S. F. Akogun, Y. Zhang, Y. X. Sun, X. Y. Dong, Sensor. Actuat. B: Chem., 238, 723-734 (2017).
5. J. H. Hu, Y. Sun, J. Qi, Q. Li, T. B. Wei, Spectrochim. Acta A, 175, 125-133 (2017).
6. F. Wang, Y. L. Xu, S. O. Aderinto, H. P. Peng, H. Zhang, H. L. Wu, J. Photochem. Photobiol. A, 332, 273-282 (2017).
7. W. K. Dong, X. L. Li, L. Wang, Y. Zhang, Y. J. Ding, Sensor. Actuat. B: Chem., 229, 370-378 (2016).
8. Y. L. Xu, S. S. Mao, H. P. Peng, F. Wang, H. Zhang, S. O. Aderinto, H. L. Wu, J. Lumin., 192, 56-63 (2017).
9. S. Thavornpradit, J. Sirirak, N. Wanichacheva, J. Photochem. Photobiol. A, 330, 55-63 (2016).
10. C. Barranguet, F. P. van den Ende, M. Rutgers, A. M. Breure, M. Greijdanus, J. J. Sinke, W. Admiraal, Environ. Toxicol. Chem., 22, 1340-1349 (2003).
11. J. Liu, Y. Lu, J. Am. Chem. Soc.,129, 9838-9839 (2007).
12. Y. Sun, J. H. Hu, J. Qi, J. B. Li, Spectrochim. Acta A, 167, 101-105 (2016).
13. R. Kramer, Angew. Chem. Int. Edit., 37, 772-773 (1998).
14. G. L. Millhauser, Acc. Chem. Res., 37, 79-85 (2004).
15. E. Gaggelli, H. Kozlowski, D. Valensin, G. Valensin, Chem. Rev., 106, 1995-2044 (2006).
16. W. Y. Lin, L. Yuan, W. Tan, J. B. Feng, L. L. Long, Chem. Eur. J., 15, 1030-1035 (2009).
17. R. Bergonzi, L. Fabbrizzi, M. Licchelli, C. Mangano, Coord. Chem. Rev., 170, 31-46 (1998).
18. Q. T. Meng, Y. Shi, C. P. Wang, H. M. Jia, X. Gao, R. Zhang, Y. F. Wang, Z. Q. Zhang, Org. Biomol. Chem., 13, 2918-2926 (2015).
19. R. Zhang, X. J. Yu, Y. J. Yin, Z. Q. Ye, G. L. Wang, J. L. Yuan, Anal. Chim. Acta, 691, 83-88 (2011).
20. M. H. Lim, B. A. Wong, W. H. Pitcock, Jr., D. Mokshagundam, M. H. Baik, S. J. Lippard, J. Am. Chem. Soc., 128, 14364-14373 (2006).
21. E. B. Veale, J. A. Kitchen, T. Gunnlaugsson, Supramol. Chem., 25, 101-108 (2013).
22. Z. Xu, J. Yoon, D. R. Spring, Chem. Commun., 46, 2563-2565 (2010).
23. N. Singh, N. Kaur, B. McCaughan, J. F. Callan, Tetrahedron Lett., 51, 3385-3387 (2010).
24. J. Huang, Y. Xu, X. Qian, Dalton Ttans., 1761-1766 (2009).
25. H. L. Wu, S. O. Aderinto, Y. L. Xu, H. Zhang, X. Y. Fan, J. Appl. Spectrosc., 84, 25-30 (2017).
26. E. L. Que, D. W. Domaille, C. J. Chang, Chem. Rev., 108, 1517-1549 (2008).
27. Y. L. Xu, S. O. Aderinto, H. L. Wu, H. P. Peng, H. Zhang, J. W. Zhang, X. Y. Fan, Z. Naturforsch. B, 72, 35-41 (2017).
28. S. O. Aderinto, Y. L. Xu, H. P. Peng, F. Wang, H. L. Wu, X. Y. Fan, J. Fluoresc., 27, 79-87 (2017).
29. Y. Gao, Y. Li, X. Yang, F. He, J. Huang, M. Jiang, Z. Zhou, H. Chen, RSC Adv., 5, 80110-80117 (2015).
30. Y. Zhang, X. Guo, X. Tian, A. Liu, L. Jia, Sensor. Actuat. B: Chem., 218, 37-41 (2015).
31. H. L. Wu, H. P. Peng, F. Wang, H. Zhang, C. G. Chen, J. W. Zhang, Z. H. Yang, J. Appl. Spectrosc., 83, 931-937 (2017).
32. J. Wang, Y. Xiao, Z. Zhang, X. Qian, Y. Yang, Q. Xu, J. Mater. Chem., 15, 2836-2839 (2005).
33. S. O. Aderinto, H. Zhang, H. L. Wu, C. Y. Chen, J. W. Zhang, H. P. Peng, Z. H. Yang, F. Wang, Color. Technol., 133, 40-49 (2017).
34. H. L. Wu, C. Y. Chen, H. Zhang, H. P. Peng, F. Wang, Z. H. Yang, J. W. Zhang, Chem. Pap., 70, 685-694 (2016).
35. N. I. Georgiev, V. B. Bojinov, N. Marinova, Sensor. Actuat. B: Chem., 150, 655-666 (2010).
36. D. Staneva, I. Grabchev, J.-P. Soumillion, V. Bojinov, J. Photochem. Photobiol. A, 189, 192-197 (2007).
37. H. P. Peng, K. S. Shen, S. S. Mao, X. K. Shi, Y. L. Xu, S. O. Aderinto, H. L. Wu, J. Fluoresc., 27, 1191-1200 (2017).
38. H. L. Wu, C. P. Wang, J. W. Zhang, Y. H. Zhang, C. Y. Chen, Z. H. Yang, X. Y. Fan, Z. Naturforsch. B, 70, 863-869 (2015).
39. X. Poteau, A. I. Brown, R. G. Brown, C. Holmes, D. Matthew, Dyes Pigments, 47, 91-105 (2000).
40. X. Sun, G. Kim, Y. Xu, J. Yoon, T. D. James, Chem. Plus Chem., 81, 30-34 (2016).
41. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New York (1999).
42. O. Stern, M. Volmer, Z. Phys., 20, 183 (1919).
43. P. Job, Ann. Chim. Appl., 9, 113-203 (1928).
Review
For citations:
Shen K., Mao S., Shi X., Opeyemi Aderinto S., Xu Y., Wu H. DEVELOPMENT OF A NEW 4-AMINO-1,8-NAPHTHALIMIDE DERIVATIVE AS A FLUORESCENT PROBE FOR MONITORING THE DIVALENT COPPER ION. Zhurnal Prikladnoii Spektroskopii. 2018;85(4):612-619. (In Russ.)
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