Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu2+

doi:10.6023/cjoc201704010

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2640-2646.DOI: 10.6023/cjoc201704010 Previous Articles Next Articles

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新型基于咔唑-氨基硫脲席夫碱识别Cu²⁺的探针

李英俊^a, 张楠^a, 靳焜^b, 许永廷^a, 王思远^a, 周晓霞^a

a 辽宁师范大学化学化工学院大连 116029;
b 大连理工大学精细化工国家重点实验室大连 116012

收稿日期:2017-04-09 修回日期:2017-06-20 发布日期:2017-07-04
通讯作者: 李英俊 E-mail:chemlab.lnnu@163.com
基金资助:
辽宁省自然科学基金（No.20102126）资助项目.

Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu²⁺

Li Yingjun^a, Zhang Nan^a, Jin Kun^b, Xu Yongting^a, Wang Siyuan^a, Zhou Xiaoxia^a

a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012

Received:2017-04-09 Revised:2017-06-20 Published:2017-07-04
Contact: 10.6023/cjoc201704010 E-mail:chemlab.lnnu@163.com
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No.20102126).

1. Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu²⁺.PDF(3463KB)

Abstract

Three novel carbazole-thiosemicarbazides based Schiff-base were synthesized. The recognition ability of representive 2-((N-heptane-carbazol-3-yl)methylidene)hydrazine carbothioamide (L₂) to metal ions was investigated by naked-eye, UV-Vis, fluorescence and mass spectra. The experimental results showed that this compound had a good water solubility and can be investigated in DMSO-H₂O (V:V=6:4, Tris-HCl buffer, pH=7.0). The compound L₂ in the DMSO-H₂O displayed a dis-tinct color change from colorless to yellow upon the addition of Cu²⁺, other metal ions did not induce significant colour changes, which indicated that Schiff base L₂ can be used as a probe with naked eye detection for Cu²⁺. The fluorescence spectra showed that the probe L₂ was a high selective and sensitive "turn-off" fluorescence probe for Cu²⁺ in DMSO-H₂O (V:V=6:4, Tris-HCl buffer, pH=7.0). The association constant between the probe L₂ and Cu²⁺ was detected to be 3.42×10⁴ L·mol^-1, and the detection limit was calculated to be 8.96×10^-6 mol·L^-1. MS analysis showed a 1:1 binding stoichiometry between Cu²⁺ and L₂. The detection limit of L₂ for Cu²⁺ was far lower than the maximum allowable level of World Health Organization (WHO) limit (20 μmol·L^-1) for drinking water.

Key words: carbazole, thiosemicarbazide, Schiff base, naked-eye recognition, Cu²⁺ fluorescence probe

Cite this article

Li Yingjun, Zhang Nan, Jin Kun, Xu Yongting, Wang Siyuan, Zhou Xiaoxia. Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu²⁺[J]. Chin. J. Org. Chem., 2017, 37(10): 2640-2646.

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[1] Zhan, S. S.; Wu, Y. G.; Wang, L. M.; Zhan, X. J.; Liu, P. Biosens. Bioelectron. 2016, 86, 353.
[2] Lee, S. Y.; Bok, K. H.; Kim, J. A.; Kim, S. Y.; Kim, C. Tetrahe-dron 2016, 72, 5563.
[3] Zhou, H. T.; Sun, L.; Chen, W.; Tian, G. J.; Chen, Y.; Li, Y. R.; Su, J. H. Tetrahedron 2016, 72, 2300.
[4] Kundu, A.; Hariharan, P. S.; Prabakaran, K.; Anthony, S. P. Sens. Actuators, B:Chem. 2015, 206, 524.
[5] Yang, J. Y.; Chen, L. H.; Zheng, Y. Z.; Dong, X. Y.; Raghunandhan, R.; So, P. L.; Chan, C. C. Sens. Actuators, B:Chem. 2016, 230, 353.
[6] Qin, J. C.; Fan, L.; Yang, Z. Y. Sens. Actuators, B:Chem. 2016, 228, 156.
[7] Feng, Y.; Lia, D. X.; Wang, Q.; Wang, S. X.; Meng, X. M.; Shao, Z. L.; Zhu, M. Z.; Wang, X. Sens. Actuators, B:Chem. 2016, 225, 572.
[8] Zhou, Y. Y.; Tang, L.; Zeng, G. M.; Zhang, C.; Zhang, Y.; Xie, X. Sens. Actuators, B:Chem. 2016, 223, 280.
[9] Kandasamy, K.; Ganesabaskaran, S.; Pachamuthu, M. P.; Maheswari, R.; Ramanathan, A. Spectrochim. Acta, Part A 2015, 150, 34.
[10] Samanta, S.; Samanta, P. K.; Dutta, S.; Biswas, P. Spectrochim. Acta, Part A 2015, 147, 262.
[11] Xu, W. J.; Qi, D. Q.; You, J. Z.; Hu, F. F.; Bian, J. Y.; Yang, C. X.; Huang, J. J. Mol. Struct. 2015, 1091, 133.
[12] Wang, E. Z.; Zhou, Y. M.; Huang, Q.; Pang, L. F.; Qiao, H.; Yu, F.; Gao, B.; Zhang, J. L.; Min, Y. H.; Ma, T. S. Spectrochim. Acta, Part A 2016, 152, 327.
[13] Hu, Y.; Zhang, J.; Lv, Y. Z.; Huang, X. H.; Hu, S. L. Spectrochim. Acta, Part A 2016, 157, 164.
[14] Bekhradnia, A.; Domehri, E.; Khosravi, M. Spectrochim. Acta, Part A 2016, 152, 18.
[15] Diao, H. P.; Niu, W. P.; Liu, W.; Feng, L. H.; Xie, J. Spectrochim. Acta, Part A 2017, 170, 65.
[16] Li, Y. J.; Li, J. Y.; Xu, Y. T.; Jin, K.; Cao, X. Chin. J. Org. Chem. 2017, 37, 896(in Chinese). (李英俊, 李继阳, 许永廷, 靳焜, 曹欣, 有机化学, 2017, 37, 896.)
[17] Xiong, J. J.; Huang, P. C.; Zhang, C. Y.; Wu, F. Y. Sens. Actuators, B:Chem. 2016, 226, 30.
[18] Feng, L.; Shi, W.; Ma, J. C.; Chen, Y. B.; Kui, F.; Hui, Y. H.; Xie, Z. F. Sens. Actuators, B:Chem. 2016, 237, 563.
[19] Liu, J. L.; Meng, X.; Duan, H. D.; Xu, T.; Ding, Z. Y.; Liu, Y.; Lucia, L. Sens. Actuators, B:Chem. 2016, 227, 296.
[20] Vikneswaran, R.; Syafiq, M. S.; Eltayeb, N. E.; Kamaruddin, M. N.; Ramesh, S.; Yahya, R. Spectrochim. Acta, Part A 2015, 150, 175.
[21] Ganjali, M. R.; Hosseini, M.; Motalebi, M.; Sedaghat, M.; Mizani, F.; Faridbod, F.; Norouzi, P. Spectrochim. Acta, Part A 2015, 140, 283.
[22] Zhang, C. H.; Gao, B. Z.; Zhang, Q. Y.; Zhang, G. M.; Shuang, S. M.; Dong, C. Talanta 2016, 154, 278.
[23] You, G. R.; Lee, J. J.; Choi, Y. W.; Lee, S. Y.; Kim, C. Tetrahedron 2016, 72, 875.
[24] Zhu, W. J.; Yang, L. L.; Fang, M.; Wu, Z. Y.; Zhang, Q.; Yin, F. F.; Huang, Q.; Li, C. J. Lumin. 2015, 158, 38.
[25] Jagadeeswari, S.; Paramaguru, G.; Thennarasu, S.; Renganathan, R. J. Mol. Struct. 2014, 1060, 191.
[26] Jagadeeswari, S.; Paramaguru, G.; Thennarasu, S.; Renganathan, R. J. Mol. Struct. 2014, 1060, 191.
[27] Ramkumar, S.; Manoharan, S.; Anandan, S. Dyes Pigm. 2012, 94, 503.
[28] Budreckiene, R.; Buika, G.; Grazulevicius, J. V.; Jankauskas, V.; Staniskiene, B. J. Photochem. Photobiol., A 2006, 181, 257.

新型基于咔唑-氨基硫脲席夫碱识别Cu²⁺的探针

Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu²⁺

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新型基于咔唑-氨基硫脲席夫碱识别Cu2+的探针