DOI QR코드

DOI QR Code

A New Rhodamine B Hydrazide Hydrazone Derivative for Colorimetric and Fluorescent "Off-On" Recognition of Copper(II) in Aqueous Media

  • Tang, Lijun (Department of Chemistry, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University) ;
  • Guo, Jiaojiao (Department of Chemistry, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University) ;
  • Wang, Nannan (Department of Chemistry, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University)
  • 투고 : 2012.10.02
  • 심사 : 2012.10.24
  • 발행 : 2013.01.20

초록

A new Rhodamine B hydrazide hydrazone 1 has been synthesized and investigated as a colorimetric and fluorescent "off-on" sensor for the recognition of $Cu^{2+}$ in $CH_3CN/H_2O$ (1:1, v/v, HEPES 10 mM, pH = 7.0) solution. Sensor 1 displayed highly selective, sensitive and rapid recognition behavior toward $Cu^{2+}$ among a range of biologically and environmentally important metal ions. Sensor 1 bind $Cu^{2+}$ via a 1:1 stoichiometry with an association constant of $1.92{\times}10^6\;M^{-1}$, and the detection limit is evaluated to be $7.96{\times}10^{-8}\;M$. The $Cu^{2+}$ recognition event is reversible and is barely interfered by other coexisting metal ions.

키워드

참고문헌

  1. Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N. Coord. Chem. Rev. 2000, 205, 59. https://doi.org/10.1016/S0010-8545(00)00242-3
  2. Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3. https://doi.org/10.1016/S0010-8545(00)00246-0
  3. Zhang, J.-F.; Zhou, Y.; Yoon, J.; Kim, J. S. Chem. Soc. Rev. 2011, 40, 3416. https://doi.org/10.1039/c1cs15028f
  4. Basabe-Desmonts, L.; Reinhoudt, D. N.; Crego-Calama, M. Chem. Soc. Rev. 2007, 36, 993. https://doi.org/10.1039/b609548h
  5. Deraeve, C.; Boldron, C.; Maraval, A.; Mazarguil, H.; Gornitzka, H.; Vendier, L.; Pitie, M.; Meunier, B. Chem. Eur. J. 2008, 14, 682. https://doi.org/10.1002/chem.200701024
  6. Bruijn, L. I.; Miller, T. M.; Cleveland, D. W. Annu. Rev. Neurosci. 2004, 27, 723. https://doi.org/10.1146/annurev.neuro.27.070203.144244
  7. Hahn, S. H.; Tanner, M.; Danke, D.; Gahl, W. A. Biochem. Mol. Med. 1995, 54, 142. https://doi.org/10.1006/bmme.1995.1021
  8. Zietz, B. P.; Vergara, J. Dassel de; Dunkelberg, H. Environ. Res. 2003, 92, 129. https://doi.org/10.1016/S0013-9351(03)00037-9
  9. Zhao, Y.; Zhang, X.-B.; Han, Z.-X.; Qiao, L.; Li, C.-Y.; Jian, L.-X.; Shen, G.-L.; Yu, R.-Q. Anal. Chem. 2009, 81, 7022. https://doi.org/10.1021/ac901127n
  10. Jung, H. S.; Kwon, P. S.; Lee, J. W.; Kim, J. I.; Hong, C. S.; Kim, J. W.; Yan, S.; Lee, J. Y.; Lee, J. H.; Joo, T. J. Am. Chem. Soc. 2009, 131, 2008. https://doi.org/10.1021/ja808611d
  11. Yu, M.; Shi, M.; Chen, Z.; Li, F.; Li, X.; Gao, Y.; Xu, J.; Yang, H.; Zhou, Z.; Yi, T. Chem. Eur. J. 2008, 14, 6892. https://doi.org/10.1002/chem.200800005
  12. Xu, Z.; Yoon, J.; Spring, D. R. Chem. Comm. 2010, 46, 2563. https://doi.org/10.1039/c000441c
  13. Xu, Z.; Zhang, L.; Guo, R.; Xiang, T.; Wu, C.; Zheng, Z.; Yang, F. Sens. Actuators B 2011, 156, 546. https://doi.org/10.1016/j.snb.2011.01.066
  14. Mashraqui, S. H.; Chandiramani, M.; Betkar, R.; Ghorpade, S. Sens. Actuators B 2010, 150, 574. https://doi.org/10.1016/j.snb.2010.08.037
  15. Xie, P.; Guo, F.; Li, D.; Liu, X.; Liu, L. J. Lumin. 2011, 131, 104. https://doi.org/10.1016/j.jlumin.2010.09.021
  16. Chen, X.; Wang, J.; Cui, J.; Xu, Z.; Peng, X. Tetrahedron 2011, 67, 4869. https://doi.org/10.1016/j.tet.2011.05.001
  17. Zhu, H.; Fan, J.; Lu, J.; Hu, M.; Cao, J.; Wang, J.; Li, H.; Liu, X.; Peng, X. Talanta 2012, 93, 55. https://doi.org/10.1016/j.talanta.2012.01.024
  18. Ramette, R. W.; Sandell, E. B. J. Am. Chem. Soc. 1956, 78, 4872. https://doi.org/10.1021/ja01600a017
  19. Kim, H. N.; Lee, M. H.; Kim, H. J.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1465. https://doi.org/10.1039/b802497a
  20. Chen, X.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Chem. Rev. 2011, 112, 1910.
  21. Liu, W.-Y.; Li, H.-Y.; Zhao, B.-X.; Miao, J.-Y. Org. Biomol. Chem. 2011, 9, 4802. https://doi.org/10.1039/c1ob05358b
  22. Gisch, N.; Balzarini, J.; Meier, C. J. Med. Chem. 2008, 51, 6752. https://doi.org/10.1021/jm800853p
  23. Zhou, Y.; Wang, F.; Kim, Y.; Kim, S. J.; Yoon, J. Org. Lett. 2009, 11, 4442. https://doi.org/10.1021/ol901804n
  24. Yu, C.; Zhang, J.; Wang, R.; Chen, L. Org. Biomol. Chem. 2010, 8, 5277. https://doi.org/10.1039/c0ob00553c
  25. Weerasinghe, A. J.; Abebe, F. A.; Sinn, E. Tetrahedron Lett. 2011, 52, 5648. https://doi.org/10.1016/j.tetlet.2011.08.092
  26. Sun, C.; Chen, J.; Ma, H.; Liu, Y.; Zhang, J.; Liu, Q. Sci. China, Ser. B: Chem. 2011, 54, 1101. https://doi.org/10.1007/s11426-011-4275-1
  27. Xiang, Y.; Tong, A.; Jin, P.; Ju, Y. Org. Lett. 2006, 8, 2863. https://doi.org/10.1021/ol0610340
  28. Dong, M.; Ma, T.-H.; Zhang, A.-J.; Dong, Y.-M.; Wang, Y.-W.; Peng, Y. Dyes Pigm. 2010, 87, 164. https://doi.org/10.1016/j.dyepig.2010.03.015
  29. Anthoni, U.; Christophersen, C.; Nielsen, P.; Püschl, A.; Schaumburg, K. Struct. Chem. 1995, 6, 161. https://doi.org/10.1007/BF02286443
  30. Shiraishi, Y.; Sumiya, S.; Kohno, Y.; Hirai, T. J. Org. Chem. 2008, 73, 8571. https://doi.org/10.1021/jo8012447
  31. Wang, L.; Yan, J.; Qin, W.; Liu, W.; Wang, R. Dyes Pigm. 2012, 92, 1083. https://doi.org/10.1016/j.dyepig.2011.07.010
  32. Kim, H. N.; Nam, S.-W.; Swamy, K. M. K.; Jin, Y.; Chen, X.; Kim, Y.; Kim, S. J.; Park, S.; Yoon, J. Analyst 2011, 136, 1339. https://doi.org/10.1039/c0an00804d
  33. Zhang, L.-F.; Zhao, J.-L.; Zeng, X.; Mu, L.; Jiang, X.-K.; Deng, M.; Zhang, J.-X.; Wei, G. Sens. Actuators B. 2011, 160, 662. https://doi.org/10.1016/j.snb.2011.08.045
  34. Zhu, H.; Fan, J.; Lu, J.; Hu, M.; Cao, J.; Wang, J.; Li, H.; Liu, X.; Peng, X. Talanta 2012, 93, 55. https://doi.org/10.1016/j.talanta.2012.01.024
  35. He, G.; Zhang, X.; He, C.; Zhao, X.; Duan, C. Tetrahedron 2010, 66, 9762. https://doi.org/10.1016/j.tet.2010.09.043
  36. Lin, W.; Yuan, L.; Cao, Z.; Feng, Y.; Long, L. Chem. Eur. J. 2009, 15, 5096. https://doi.org/10.1002/chem.200802751
  37. Shortreed, M.; Kopelman, R.; Kuhn, M.; Hoyland, B. Anal. Chem. 1996, 68, 1414.
  38. Kim, M. H.; Jang, H. H.; Yi, S.; Chang, S. K.; Han, M. S. Chem. Commun. 2009, 4838.
  39. Mei, L.; Xiang, Y.; Li, N.; Tong, A. Talanta 2007, 72, 1717. https://doi.org/10.1016/j.talanta.2007.02.002
  40. Zhao, M.; Yang, X.-F.; He, S.; Wang, L. Sens. Actuators B 2009, 135, 625. https://doi.org/10.1016/j.snb.2008.10.044
  41. Yang, Y.; Gao, W.; Sheng, R.; Wang, W.; Liu, H.; Yang, W.; Zhang, T.; Zhang, X. Spectrochim. Acta, Part A 2011, 81, 14. https://doi.org/10.1016/j.saa.2011.05.016
  42. Lan, G. Y.; Huang, C. C.; Chang, H. T. Chem. Commun. 2010, 46, 1257. https://doi.org/10.1039/b920783j

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