Chinese Journal of Organic Chemistry >
Synthesis and Properties of Rhodamine B Derivative for Recognition of Cu2+ and Hg2+
Received date: 2012-04-27
Revised date: 2012-05-23
Online published: 2012-06-06
Supported by
Project supported by the Science and Technology Department of Sichuan Province (No. 2009JY0078), the Education Department of Sichuan Province (No.11ZA154) and the Science and Technology Bureau of Leshan Town (No. 2011SZD107).
A novel rhodamine B derivative L was synthesized facilely by the condensation reaction of rhodamine B hydrazide and 2-hydroxyquinoline-3-carbaldehyde, and its structure was characterized by 1H NMR, MS techniques and elemental analysis. The recognition properties of the target compound L with metal ions had been investigated in CH3CN-H2O (V∶V＝1∶1) solution by the ultraviolet spectrophotometry and the fluorescence spectrophotometry. The results showed that the probe L exhibited the selective colorimetric recognition of Cu2+ and the fluorogenic recognition of Hg2+. Upon the addition of Cu2+ or Hg2+, the spirolactam ring of probe L was opened and 1∶1 ligand-copper complex or 1∶2 ligand-mercury complex was formed, and both of the Cu2+ and Hg2+ recognition processes were proven to be a revisible process.
Chen Jiaxuan , Tian Yi , Xiang Qingxiang , Zhang Liqun , Xiong Junru . Synthesis and Properties of Rhodamine B Derivative for Recognition of Cu2+ and Hg2+[J]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1930 -1935 . DOI: 10.6023/cjoc201204031
[1] Tapiero, H.; Townsend, D. M.; Tew, K. D. Biomed. Pharmacother. 2003, 57, 386.
[2] Waggoner, D. J.; Bartnikas, T. B.; Gitlin, J. D. Neurobiol. Dis. 1999, 6, 221.
[3] Vulpe, C.; Levinson, B.; Whitney, S.; Packman, S.; Gitschier, J. Nat. Genet. 1993, 3, 7.
[4] Lee, J. C.; Gray, H. B.; Winkler, J. R. J. Am. Chem. Soc. 2008, 130, 6898.
[5] Renzoni, A.; Zino, F.; Franchi, E. Environ. Res. 1998, 77, 68.
[6] Boening, D. W. Chemosphere 2000, 40, 1335.
[7] Harada, M.; Minamata, D. Crit. Rev. Toxicol. 1995, 25, 1.
[8] Kim, H. N.; Lee, M. H.; Kim, H. J.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1465.
[9] Dujols, V.; Ford, F.; Czarnik, A. W. J. Am. Chem. Soc. 1997, 119, 7386.
[10] Li, N.; Liu, M.; Yin, W.-T.; Yang, Z.; Li, J.-L.; Shi, Z. Chin. J. Org. Chem. 2011, 31, 39 (in Chinese).
(李娜, 刘美玲, 尹文婷, 杨征, 李剑利, 史真, 有机化学, 2011, 31, 39.)
[11] Sun, W.; Hu, D.-Y.; Wu, Z.-B.; Song, B.-A.; Yang, S. Chin. J. Org. Chem. 2011, 31, 997 (in Chinese).
(孙伟, 胡德禹, 吴志兵, 宋宝安, 杨松, 有机化学, 2011, 31, 997.)
[12] Mariana, B.; Carlos, A. M. A.; José, M. G. M. Chem. Soc. Rev. 2009, 38, 2410.
[13] Wang, L. N.; Yan, J. X.; Qin, W. W.; Liu, W. S.; Wang, R. Dyes Pigm. 2012, 92, 1083.
[14] 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.
[15] Tang, L. J.; Li, F. F.; Liu, M. H.; Nandhakumar, R. Spectrochim. Acta, A 2011, 78, 1168.
[16] Weerasinghe, A. J.; Abebe, F. A.; Sinn, E. Tetrahedron Lett. 2011, 52, 5648.
[17] Xiang, Y.; Tong, A.-J.; Jin, P.-Y.; Ju, Y. Org. Lett. 2006, 8, 2863.
[18] Zhou, Y.; Wang, F.; Kim, Y.; Kim, S.-J.; Yoon, J. Org. Lett. 2009, 11, 4442.
[19] Jiang, L.; Wang, L.; Zhang, B.; Yin, G.; Wang, R.-Y. Eur. J. Inorg. Chem. 2010, 28, 4438.
[20] Dong, M.; Ma, T.-H.; Zhang, A.-J.; Dong, Y.-M.; Wang, Y.-W.; Peng, Y. Dyes Pigm. 2010, 87, 164.
[21] Coronado, E.; Galan-Mascaros, J. R.; Marti-Gastaldo, C.; Palomares, E.; Durrant, J. R.; Vilar, R.; Gratzel, M.; Nazeeruddin, M. K. J. Am. Chem. Soc. 2005, 127, 12351. Srivastava, A.; Singh, R. M. Indian J. Chem., B 2005, 44, 1868.
/
| 〈 |
|
〉 |
