SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 11: 3757 - 3765

DOI: https://doi.org/10.6023/cjoc202204026

研究论文

一种基于氟硼二吡咯(BODIPY)衍生物的高选择性“Off-On”型Cu2＋比色-荧光探针

  • 赵小龙 ,
  • 李宇晴 ,
  • 郭亮武 ,
  • 冉启元 ,
  • 吴会慧 ,
  • 张祯 ,
  • 苏瀛鹏 ,
  • 周鹏鑫 ,
  • 燕娜
展开
  • a西北师范大学化学化工学院 教育部生态环境相关高分子重点实验室 兰州 730070

收稿日期: 2022-04-11

  修回日期: 2022-07-06

  网络出版日期: 2022-07-21

基金资助

甘肃省高等学校产业支撑计划(2021CYZC-17); 甘肃省自然科学基金(21JR1RA227); 国家自然科学基金(21462039)

收起

A Highly Selective and High-Contrast Colorimetric “Off-On” Chemosensor for Cu2＋ Based on Boron-Dipyrromethene (BODIPY) Derivatives

  • Xiaolong Zhao ,
  • Yuqing Li ,
  • Liangwu Guo ,
  • Qiyuan Ran ,
  • Huihui Wu ,
  • Zhen Zhang ,
  • Yingpeng Su ,
  • Pengxin Zhou ,
  • Na Yan
Expand
  • aKey Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
    b兰州大学药学院 兰州 730000
*E-mail:

Received date: 2022-04-11

  Revised date: 2022-07-06

  Online published: 2022-07-21

Supported by

Gansu Provincial Industrial Support Program for Colleges(2021CYZC-17); Natural Science Foundation of Gansu Province(21JR1RA227); National Natural Science Foundation of China(21462039)

Fold

摘要

开发了一种水溶性良好的荧光增强型氟硼二吡咯(BODIPY)探针BDP-2Z. 在较宽的pH范围(pH=3.0~12.0)内探针对Cu2＋表现出低检测限、快速响应、高灵敏度和选择性等优势. Cu2＋引起的颜色和荧光对比非常显著, 能实现 Cu2＋的可视化检测. 通过柱层析法分离得到识别过程的水解产物, 并利用紫外和荧光光谱、质谱分析证实了识别机制. 此外, 在真实水样中的快速裸眼识别扩展了其在环境检测方面的应用.

关键词： 水溶性; 可视化; BODIPY衍生物; 荧光增强

本文引用格式

赵小龙 , 李宇晴 , 郭亮武 , 冉启元 , 吴会慧 , 张祯 , 苏瀛鹏 , 周鹏鑫 , 燕娜 . 一种基于氟硼二吡咯(BODIPY)衍生物的高选择性“Off-On”型Cu2＋比色-荧光探针[J]. 有机化学, 2022 , 42(11) : 3757 -3765 . DOI: 10.6023/cjoc202204026

Abstract

Based on the platform of boron-dipyrromethene (BODIPY) derivatives, a fluorescence turn-on probe BDP-2Z was rationally designed and synthesized with good water-solubility. With high sensitivity and selectivity for Cu2＋ over other competitive ions, the reaction-based probe showed low detection limit and fast response in a wide pH range (pH=3.0~12.0). The contrast of color and fluorescence caused by Cu2＋ was remarkable so much so that it was easily to distinguish Cu2＋ from other ions with naked-eye detection. Along with adding of Cu2＋, a blue shift of maximum absorption was observed from 548 nm to 496 nm, the corresponding solution color changed obviously from purple to light orange, and the fluorescence is enhanced by nearly 5-fold. Furthermore, the recognition mechanism was confirmed by UV-Vis, fluorescence spectra, and mass spectral analysis. The identified product of recognition process was even obtained by original silica gel column chromatography separation method. Also, the rapidly naked-eye application in real water samples provides an alternative to extension environmental detection.

Key words： water-soluble; naked-eye; BODIPY derivatives; fluorescence turn-on

参考文献

[1]
Kirsipuu, T.; Zadoroznaja, A.; Smirnova, J.; Friedemann, M.; Plitz, T.; Tougu, V.; Palumaa, P. Sci. Rep. 2020, 10, 5686.
[2]
Rakshit, A; Khatua, K.; Shanbhag, V.; Comba, P.; Datta, A. Chem. Sci. 2018, 9, 7916.
[3]
Zhang, J.; Duan, D.; Xu, J.; Fang, J. ACS Appl. Mater. Interfaces 2018, 10, 33010.
[4]
Erfanian, A.; Mirhosseini, H.; Rasti, B.; Hair-Bejo, M.; Mustafa, S. B.; Manap, M. Y. A. J. Agric. Food Chem. 2015, 63, 5795.
[5]
Horvath, I.; Blockhuys, S.; Ulskis, D.; Holgersson, S.; Kumar, R.; Burmann, B. M.; Wittung Stafshede, P. ACS Chem. Neurosci. 2019, 10, 4659.
[6]
Zhao, J.; Shi, Q.; Tian, H.; Li, Y.; Liu, Y.; Xu, Z.; Robert, A.; Liu, Q.; Meunier, B. ACS Chem. Neurosci. 2021, 12, 140.
[7]
Wang, X.; Chen, X.; Zhou, R.; Hu, P.; Huang, K.; Chen, P. Anal. Chem. 2021, 93, 3889.
[8]
Kumar, R.; Sharma, A.; Singh, H.; Suating, P.; Kim, H. S.; Sunwoo, K.; Shim, I.; Gibb, B. C.; Kim, J. S. Chem. Rev. 2019, 119, 9657.
[9]
W. Li, ; Gong, X..; Fan, X.; Yin, S.; Su, D.; Zhang, X.; Yuan, L. Chin. Chem. Lett. 2019, 30, 1775.
[10]
Chandra, R.; Ghorai, A.; Patra, G. K. Sens. Actuators, B 2018, 255, 701.
[11]
Li, X.; Wu, X.; Zhang, F.; Zhao, B.; Li, Y. Talanta 2019, 195, 372.
[12]
Nan, X.; Huyan, Y.; Li, H.; Sun, S.; Xu, Y. Coordin. Chem. Rev. 2021, 426, 213580.
[13]
Wang, Z.; Jia, J.; Zhang, Y.; Chao, J. Bioorg. Chem. 2022, 120, 105618.
[14]
Liu, L.; Dan, F.; Liu, W.; Lu, X.; Han, Y.; Xiao, S.; Lan, H. Sens. Actuators, B 2017, 247, 445.
[15]
Zhang, X.; Guo, X.; Yuan, H.; Jia, X.; Dai, B. Dyes Pigm. 2018, 155, 100.
[16]
Aydin, Z.; Yan, B.; Wei, Y.; Guo, M. Chem. Commun. 2020, 56, 6043.
[17]
Wang, X.; Tao, J.; Chen, X.; Yang, H. Sens. Actuators, B 2017, 244, 709.
[18]
Gharami, S.; Sarkar, D.; Acharyya, S.; Mondal, T. K. J. Fluoresc. 2016, 26, 2133.
[19]
Wang, S.; Pang, Y.; Xue, M.; Yang, Y. New J. Chem. 2021, 45, 19219.
[20]
Jiao, Y.; Zhou, L.; He, H.; Yin, J.; Gao, Q.; Wei, J.; Duan, C.; Peng, X. Talanta 2018, 184, 143.
[21]
Yang, L.; Tang, A.; Wang, P. Org. Lett. 2020, 22, 8234.
[22]
Liu, C.; Jiao, X.; He, S.; Zhao, L.; Zeng, X. Org. Biomol. Chem. 2017, 15, 3947.
[23]
Liu, K.; Marin, L.; Xiao, L.; Cheng, X. New J. Chem. 2021, 45, 22888.
[24]
Zhao, X.; Gao, C.; Li, N.; Liu, F.; Huo, S.; Li, J.; Guan, X.; Yan, N. Tetrahedron Lett. 2019, 60, 1452.
[25]
Bassan, E.; Gualandi, A.; Cozzi, P. G.; Ceroni, P. Chem. Sci. 2021, 12, 6607.
[26]
Sekhar, A. R.; Sariki, S. K.; Reddy, R. V. R.; Bisai, A.; Sahu, P. K.; Tomar, R. S.; Sankar, J. Chem. Commun. 2017, 53, 1096.
[27]
Zhang, H.; Liu, J.; Sun, Y.; Liu, M.; Guo, W. J. Am. Chem. Soc. 2020, 142, 17069.
[28]
Zhang, Y.; Zheng, X.; Zhang, L.; Yang, Z.; Chen, L.; Wang, L.; Liu, S.; Xie, Z. Org. Biomol. Chem. 2020, 18, 707.
[29]
Chen, H.; He, X.; Su, M.; Zhai, W.; Zhang, H.; Li, C. J. Am. Chem. Soc. 2017, 139, 10157.
[30]
Dunnebacke, T.; Kartha, K. K.; Wahl, J. M.; Albuquerque, R. Q.; Fernandez, G. Chem. Sci. 2020, 11, 10405.
[31]
Lu, T.; Chen, F. J. Comput. Chem. 2012, 33, 580.
[32]
Liu, Z.; Lu, T. ; Chen, Q. Carbon 2020, 165, 461.
Options
文章导航

/

〈 〉