Synthesis and Properties of Rhodamine B Derivative for Recognition of Cu2+ and Hg2+

doi:10.6023/cjoc201204031

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (10): 1930-1935.DOI: 10.6023/cjoc201204031 Previous Articles Next Articles

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罗丹明B衍生物的合成及其对Cu²⁺, Hg²⁺的识别研究

陈稼轩, 田怡, 向清祥, 张丽群, 熊俊如

乐山师范学院化学与生命科学学院乐山 614000

收稿日期:2012-04-27 修回日期:2012-05-23 发布日期:2012-06-06
通讯作者: 向清祥 E-mail:qxxiang711@163.com
基金资助:
四川省科技厅应用基础(No. 2009JY0078)、四川省教育厅重点(No. 11ZA154)和乐山市科技局重点(No. 2011SZD107)资助项目.

Synthesis and Properties of Rhodamine B Derivative for Recognition of Cu²⁺ and Hg²⁺

Chen Jiaxuan, Tian Yi, Xiang Qingxiang, Zhang Liqun, Xiong Junru

Department of Chemistry and Life Science, Leshan Normal University, Leshan 614000

Received:2012-04-27 Revised:2012-05-23 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).

1. Synthesis and Properties of Rhodamine B Derivative for Recognition of Cu²⁺ and Hg²⁺.PDF(580KB)

Abstract

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.

Key words: rhodamine B derivative, colorimetric recognition, fluorogenic recognition, metal ion

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Chen Jiaxuan, Tian Yi, Xiang Qingxiang, Zhang Liqun, Xiong Junru. Synthesis and Properties of Rhodamine B Derivative for Recognition of Cu²⁺ and Hg²⁺[J]. Chin. J. Org. Chem., 2012, 32(10): 1930-1935.

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References

[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.

罗丹明B衍生物的合成及其对Cu²⁺, Hg²⁺的识别研究

Synthesis and Properties of Rhodamine B Derivative for Recognition of Cu²⁺ and Hg²⁺

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罗丹明B衍生物的合成及其对Cu2+, Hg2+的识别研究