SIOC English
有机化学
高级检索

有机化学 >

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

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

研究论文

一种基于罗丹明B酰腙的具有高灵敏度和选择性的“Off-On”型Cu2＋荧光探针

  • 雷萌萌 ,
  • 周起航 ,
  • 杨莉 ,
  • 许志红 ,
  • 杨风岭
展开
  • a 郑州大学化学学院 郑州 450001;
    b 许昌学院化工与材料学院 河南许昌 461000

收稿日期: 2020-05-29

  修回日期: 2020-07-02

  网络出版日期: 2020-07-09

基金资助

国家自然科学基金-河南联合基金（No.U1304202）、河南省高校科技创新人才计划（No.15HASTIT002）、河南省科技厅（No.192102310295）、河南省高校重点研究计划（No.19A150046）和许昌市重点（No.2019-JC-02）资助项目.

收起

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

摘要

以5-甲酰基-3，4-二甲基吡咯-2-羧酸乙酯和罗丹明B酰肼为原料，合成了一种"Off-On"型罗丹明衍生物Cu2+荧光探针R1.探针R1对Cu2+识别具有高选择性和高灵敏度，其检出限（LOD）为0.201 μmol·L-1，此外探针R1与Cu2+作用后颜色从无色变为粉红色，可以实现Cu2+的"裸眼检测".探针R1成功用于实际水样中Cu2+的检测.

关键词： 荧光探针; 罗丹明; 吡咯; Cu2＋

本文引用格式

雷萌萌 , 周起航 , 杨莉 , 许志红 , 杨风岭 . 一种基于罗丹明B酰腙的具有高灵敏度和选择性的“Off-On”型Cu2＋荧光探针[J]. 有机化学, 2020 , 40(9) : 2798 -2803 . DOI: 10.6023/cjoc202005084

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+

参考文献

[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
文章导航

/

〈 〉