SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2798 - 2803

DOI: https://doi.org/10.6023/cjoc202005084

A Highly Sensitive and Selective “Off-On” Fluorescent Probe for Cu2+ Based on Rhodamine B Hydrazone

  • Lei Mengmeng ,
  • Zhou Qihang ,
  • Yang Li ,
  • Xu Zhihong ,
  • Yang Fengling
Expand
  • a College of Chemistry, Zhengzhou University, Zhengzhou 450001;
    b College of Chemical and Materials Engineering, Xuchang University, Xuchang, Henan 461000

Received date: 2020-05-29

  Revised date: 2020-07-02

  Online published: 2020-07-09

Supported by

Project supported by the Joint Program for Fostering Talents of National Natural Science Foundation of China and Henan Province (No. U1304202), the Program for Science and Technology Innovation Talents in Universities of Henan Province (No. 15HASTIT002), the Science and Technology Project of Henan Province (No. 192102310295), the Key Program in Universities of Henan Province (No. 19A150046), and the Key Program of Xuchang City (No. 2019-JC-02).

Fold

Abstract

Ethyl 5-formyl-3,4-dimethyl-pyrrole-2-carboxylate and rhodamine B hydrazide were used to synthesize a rhodamine derivative R1. Notably, the as-synthesized R1 displayed great sensitivity and selectivity, which was utilized to be an off-on fluorescence probe for Cu2+ detectionin mediums that contained water. Besides, the Cu2+ ions limit of detection (LOD) was 0.201 μmol·L-1, and R1 was able to sense Cu2+ by "naked-eye" according to the change in color to pink from colorless. In addition, Cu2+ detection was assessed within the actual water samples for testing the probe actual application.

Key words： fluorescent probe; rhodamine; pyrrole; Cu2+

Cite this article

Lei Mengmeng , Zhou Qihang , Yang Li , Xu Zhihong , Yang Fengling . A Highly Sensitive and Selective “Off-On” Fluorescent Probe for Cu2+ Based on Rhodamine B Hydrazone[J]. Chinese Journal of Organic Chemistry, 2020 , 40(9) : 2798 -2803 . DOI: 10.6023/cjoc202005084

References

[1] Wei, J. H.; Yi, J. W.; Han, M. L.; Li, B.; Liu, S.; Wu, Y. P.; Ma, L. F.; Li, D. S. A. Chem. Asian J. 2019, 14, 3694.
[2] Wang, H.; Qin, J.; Huang, C.; Han, Y.; Xu, W.; Hou, H. Dalton Trans. 2016, 45, 12710.
[3] Wu, X.; Guo, Z.; Wu, Y.; Zhu, S.; James, T. D.; Zhu, W. ACS Appl. Mater. Interfaces 2013, 5, 12215.
[4] Guo, Z.; Kim, G. H.; Yoon, J.; Shin, I. Nat. Protoc. 2014, 9, 1245.
[5] Ma, D. L.; Wong, S. Y.; Kang, T. S.; Ng, H. P.; Han, Q. B.; Leung, C. H. Methods 2019, 168, 3.
[6] Jung, J. H.; Lee, J. H.; Shinkai, S. Chem. Soc. Rev. 2011, 40, 4464.
[7] Patil, P.; Ajey, K. V.; Bhat, M. P.; Sriram, G.; Yu, J.; Jung, H. Y.; Altalhi, T.; Kigga, M.; Kurkuri, M. D. ChemistrySelect 2018, 3, 11593.
[8] Suo, F.; Chen, X.; Fang, H. Gong, Q.; Yu, C.; Yang, N. D.; Li, S.; Wu, Q.; Li, L.; Huang, W. Dyes Pigm. 2019, 170, 107639.
[9] Ji, Y.; Dai, F.; Zhou, B. Free Radical Biol. Med. 2018, 129, 215.
[10] Singh, N.; Paknikar, K. M.; Rajwade, J. Environ Res. 2019, 175, 367.
[11] Ogunkunle, C. O.; Jimoh, M. A.; Asogwa, N. T.; Viswanathan, K.; Vishwakarma, V.; Fatoba, P. O. Ecotoxicol. Environ. Saf. 2018, 155, 86.
[12] Donnelly, P. S.; Xiao, Z.; Wedd, A. G. Curr. Opin. Chem. Biol. 2007, 11, 128.
[13] Squitti, R.; Ghidoni, R.; Simonelli, I.; Ivanova, I. D.; Colabufo, N. A.; Zuin, M.; Benussi, L.; Binetti, G.; Cassetta, E.; Rongioletti, M.; Siotto, M. J. Trace Elem. Med. Biol. 2018, 45, 181.
[14] Gardner, B.; Dieriks, B. V.; Cameron, S.; Mendis, L. H. S.; Turner, C.; Faull, R. L. M.; Curtis, M. A. Sci. Rep. 2017, 7, 10454.
[15] Ren, D.; Liu, Y.; Liu, X.; Li, Z.; Li, H.; Yang, X. F. Sens. Actuators. B 2018, 255, 2321.
[16] Yoon, J. W.; Chang, M. J.; Hong, S.; Lee, M. H. Tetrahedron Lett. 2017, 58, 3887.
[17] Jiao, Y.; Zhou, L.; He, H.; Yin, J.; Gao, Q.; Wei, J.; Duan, C.; Peng, X. Talanta 2018, 184, 143.
[18] Jia, X.; Xiao, Z.; Hui, P.; Liu, C.; Wang, Q.; Qiu, X. He, S.; Zeng, X.; Zhao, L. Dyes Pigm. 2019, 160, 633.
[19] Kang, H.; Fan, C.; Xu, H.; Pu, G.; Liu, S. Tetrahedron 2018, 74, 4390.
[20] Zhang, J. F.; Zhou, Y.; Yoon, J.; Kim, Y.; Kim, S. J.; Kim, J. S. Org Lett. 2010, 12, 3852.
[21] Yang, Z.; She, M.; Zhang, J.; Chen, X.; Huang, Y.; Zhu, H.; Liu, P.; Li, J.; Shi Z. Sens. Actuators. B 2013, 176, 482.
[22] Yu, M.; Yuan, R.; Shi, C.; Zhou, W.; Wei, L.; Li, Z. Dyes Pigm. 2013, 99, 887.
[23] Goswami, S.; Sen, D.; Das, A. K.; Das, N. K.; Aich, K.; Fun, H. K.; Quah, C. K.; Maity, A. K.; Saha, P. Sensors. Actuators. B 2013, 183, 518.
[24] Kar, C.; Adhikari, M. D.; Ramesh, A.; Das, G. Inorg. Chem. 2013, 52, 743.
[25] Xiong, K.; Chen, J. G. Catalysis Today. 2018, 339, 289.
[26] Xu, Q.; Guo, Z. J. East China Univ. Sci. Technol. 2019, 45, 357.
[27] Yi, X.; Li, G.; Huang, L.; Chu, Y.; Liu, Z. Q.; Xia, H.; Zheng, A.; Deng, F. J. Phys. Chem. C. 2017, 121, 3887.
[28] Jr, P. A.; Liu, Y.; Palacios, M. A.; Minami, T. Wang, Z.; Nishiyabu, R. Chem.-Eur. J. 2013, 19, 8497.
[29] Wang, Y.; Wu, H.; Wu, W. N.; Li, S. J.; Xu, Z. H.; Xu, Z. Q. Fan, Y. C.; Zhao, X. L.; Liu, B. Z. Sens. Actuators. B 2018, 260, 106.
[30] Moubaraki, R.; Li, B.; Murray, K. S.; Brooker, S. Eur. J. Inorg. Chem. 2009, 19, 2851.
[31] Wang, Y.; Chang, H. Q.; Wu, W. N.; Peng, W. B.; Yan, Y. F. He, C. M.; Chen, T. T.; Zhao, X. L.; Xu, Z. Q. Sensors. Actuators B:Chem. 2016, 228, 395.
[32] Li, M.; Lv, H.; Luo, J. Z.; Miao, J. Y.; Zhao, B. X. Sens. Actuators. B 2013, 188, 1235.
[33] Ge, F.; Ye, H.; Luo, J. Z.; Wang, S.; Sun, Y. J.; Zhao, B. X.; Miao, J. Y. Sens. Actuators. B 2013, 181, 215.
[34] Huang, K.; Jiao, X.; Liu, C.; Wang, Q.; Qiu, X.; He, S. Zhao, L.; Zeng, X. Dyes Pigm. 2017, 145, 561.
[35] Artesani, A.; Binet, L.; Tana, F.; Comelli, D.; Nardo, L. D.; Nevin, A.; Touati, N.; Valentini, G.; Gourier, D. Microchem. J. 2019, 151, 104256.
[36] Pressman, J. G.; Richardson, S. D.; Speth, T. F.; Miltner, R. J. Environ. Sci. Technol. 2010, 44, 7184.
[37] Xu, Z.; Wang, H.; Hou, X.; Xu, W.; Xiang, T.; Wu, C. Sens. Actuators. B 2014, 201, 469.
[38] Dujols, V.; Ford, F.; Czarnik, A. W. J. Am. Chem. Soc. 1997, 119, 7386.
[39] Kim, H.; Rao, B. A.; Jeon, J. W.; Mallick, S.; Kang, S. M.; Choi, J. S.; Lee, C. S.; Son, Y. A. Sens. Actuators. B 2015, 210, 173.
[40] Ye, X. P.; Zhu, T. F.; Wu, W. N.; Ma, T. L.; Xu, J.; Zhang, Z. P.; Wang, Y.; Jia, L. Inorg. Chem. Commun. 2014, 47, 60.
Options
Outlines

/

〈 〉