SIOC English
有机化学
高级检索

有机化学 >

2023 , Vol. 43 >Issue 3: 809 - 825

DOI: https://doi.org/10.6023/cjoc202302015

综述与进展

反应型氟离子探针的研究进展

  • 曲衍杰 ,
  • 李亚军 ,
  • 鲍红丽
展开
  • a 福建师范大学化学与材料学院 福州 350117
    b 中国科学院福建物质结构研究所 中国科学院煤制乙二醇及相关技术重点实验室 福州 350002

收稿日期: 2023-02-14

  修回日期: 2023-02-25

  网络出版日期: 2023-03-01

基金资助

国家杰出青年科学基金(22225107); 国家自然科学基金(21871258); 国家自然科学基金(21922112)

收起

Research Progress of Reaction-Based Probes for Detecting Fluoride Ion

  • Yanjie Qu ,
  • Yajun Li ,
  • Hongli Bao
Expand
  • a College of Chemistry and Material Science, Fujian Normal University, Fuzhou 350117
    b Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002
* Corresponding author. E-mail:

Received date: 2023-02-14

  Revised date: 2023-02-25

  Online published: 2023-03-01

Supported by

National Science Fund for Distinguished Young Scholars(22225107); National Natural Science Foundation of China(21871258); National Natural Science Foundation of China(21922112)

Fold

摘要

氟离子与人的生命活动密切相关, 人体内氟离子含量过多或过少都会引起病变. 因此, 开发合适的手段检测人体内和环境中的氟离子含量是必要的. 比色法和荧光检测法由于具有选择性高、灵敏度高以及响应快速的特点而备受关注. 围绕反应型氟离子探针进行了综述, 根据反应类型分为氟离子与有机硼化物结合型探针、氟离子诱导Si—C键断裂型探针、氟离子诱导Si—O键断裂型探针、氟离子诱导脱氢型探针和氟离子诱导P—O键断裂型探针5种. 不仅对探针的检测方法进行了介绍, 而且对于某些示例的作用机理也进行了阐述.

关键词： 氟离子; 比色和荧光检测法; 反应型探针; 生物成像; 环境检测

本文引用格式

曲衍杰 , 李亚军 , 鲍红丽 . 反应型氟离子探针的研究进展[J]. 有机化学, 2023 , 43(3) : 809 -825 . DOI: 10.6023/cjoc202302015

Abstract

Fluoride ion is closely related to human life activities. Excessive or too little fluoride ions in human body will cause pathological changes. Therefore, it is necessary to develop appropriate measures to detect the fluoride ion content in human body and environment. Colorimetry and fluorescence detection have attracted much attention due to their high selectivity, high sensitivity and fast response. Herein, reaction-based fluoride ion probes are introduced. According to the reaction mechanisms, these probes can be divided into five types: interactions between fluoride ion and boronic acid derivatives, fluoride ion-promoted cleavage of Si—C bond, fluoride ion-promoted cleavage of Si—O bond, fluoride ion-induced dehydrogenation, fluoride ion-promoted cleavage of P—O bond. Not only the detection method of the probe is introduced, but also the action mechanism of some examples is described.

Key words： fluoride ion; colorimetric and fluorescent detection; reaction-based probe; bio-imaging; environmental detection

参考文献

[1]
Newbrun, E. J. Public Health Dent. 2010, 70, 227.
[2]
Kleerekoper, M. Endocrinol. Metab. Clin. North Am. 1998, 27, 441.
[3]
Matsui, H.; Morimoto, M.; Horimoto, K.; Nishimura, Y. Toxicol. In Vitro 2007, 21, 1113.
[4]
Han, J.; Zhang, J.; Gao, M.; Hao, H.; Xu, X. Dyes Pigm. 2019, 162, 412.
[5]
Zhou, Y.; Zhang, J.; Yoon, J. Chem. Rev. 2014, 114, 5511.
[6]
Yoon, J.; Czarnik, A. W. J. Am. Chem. Soc. 1992, 114, 5874.
[7]
Suenaga, H.; Mikarni, M.; Sandanayake, K. R. A. S.; Shinkai, S. Tetrahedron Lett. 1995, 36, 4825.
[8]
Cooper, C. R.; Spencer, N.; James, T. D. Chem. Commun. 1998, 1365.
[9]
(a) Badugu, R.; Lakowicz, J. R.; Geddes, C. D. Sens. Actuators, B 2005, 104, 103.
[9]
(b) Xu, Z.; Kim, S. K.; Han, S. J.; Lee, C.; Gabriele, K.-K.; James, T. D.; Yoon, J. Eur. J. Org. Chem. 2009, 2009, 3058.
[9]
(c) Jun, E. J.; Xu, Z.; Lee, M.; Yoon, J. Tetrahedron Lett. 2013, 54, 2755.
[9]
(d) Nishimura, T.; Xu, S.; Jiang, Y.; Fossey, J. S.; Sakurai, K.; Bull, S. D.; James, T. D. Chem. Commun. 2013, 49, 478.
[10]
Tan, W.; Zhang, D.; Zhu, D. Bioorg. Med. Chem. Lett. 2007, 17, 2629.
[11]
Nicolini, J.; Testoni, F. M.; Schuhmacher, S. M.; Machado, V. G. Tetrahedron Lett. 2007, 48, 3467.
[12]
Zhang, G.; Wang, L.; Cai, X.; Zhang, L.; Yu, J.; Wang, A. Dyes Pigm. 2013, 98, 232.
[13]
Su, Z.; Yan, X.; Liang, C.; Lin, C.; Xie, L.; Yuan, Y. Tetrahedron Lett. 2016, 57, 1250.
[14]
Zhang, Y.; Qu, Y.; Zhang, Y.; Gao, Y.; Wang, L. Chem. Eng. J. 2022, 448.
[15]
Rao, M. R.; Mobin, S. M.; Ravikanth, M. Tetrahedron 2010, 66, 1728.
[16]
Fu, L.; Jiang, F.; Fortin, D.; Harvey, P. D.; Liu, Y. Chem. Commun. 2011, 47, 5503.
[17]
Fu, L.; Wang, F.; Gao, T.; Huang, R.; He, H.; Jiang, F.; Liu, Y. Sens. Actuators, B 2015, 216, 558.
[18]
Lu, H.; Wang, Q.; Li, Z.; Lai, G.; Jiang, J.; Shen, Z. Org. Biomol. Chem. 2011, 9, 4558.
[19]
Jo, M.; Lim, J.; Miljani?, O. S. Org. Lett. 2013, 15, 3518.
[20]
Hu, R.; Feng, J.; Hu, D.; Wang, S.; Li, S.; Li, Y.; Yang, G. Angew. Chem., Int. Ed. 2010, 49, 4915.
[21]
Cao, X.; Lin, W.; Yu, Q.; Wang, J. Org. Lett. 2011, 13, 6098.
[22]
Zheng, Y.; Duan, Y.; Ji, K.; Wang, R.-L.; Wang, B. RSC Adv. 2016, 6, 25242.
[23]
Tian, X.; Tong, X.; Li, Z.; Li, D.; Kong, Q.; Yang, X. J. Agric. Food Chem. 2018, 66, 11486.
[24]
Xu, N.; Gao, H.; Wang, S.; Gai, L.; Tian, J.; Shao, X.; Lu, H. Dyes Pigm. 2022, 205. 110536
[25]
Kim, S. Y.; Hong, J.-I. Org. Lett. 2007, 9, 3109.
[26]
Wu, Z.; Tang, X. Anal. Chem. 2015, 87, 8613.
[27]
Xu, X.; Chen, Y.; Wei, L.; Mao, W.; Lin, F.; Zhou, X. Anal. Methods 2016, 8, 245.
[28]
Zhao, Z.; Bi, X.; Mao, W.; Xu, X. Tetrahedron Lett. 2017, 58, 4129.
[29]
Xu, X.; Chen, W.; Yang, M.; Liu, X. J.; Wang, F.; Yu, R. Q.; Jiang, J. H. Talanta 2019, 204, 655.
[30]
Turan, I. S.; Akkaya, E. U. Org. Lett. 2014, 16, 1680.
[31]
Gu, B.; Dong, C.; Shen, R.; Qiang, J.; Wei, T.; Wang, F.; Lu, S.; Chen, X. Sens. Actuators, B 2019, 301. 127111
[32]
Feng, A.; Jia, Y.; Huang, L.; Wang, L.; Zhou, G.; Wang, S.; Liu, P. Spectrochim. Acta, Part A 2019, 220, 117108.
[33]
Wei, G.; Yin, J.; Ma, X.; Yu, S.; Wei, D.; Du, Y. Anal. Chim. Acta 2011, 703, 219.
[34]
Roy, A.; Kand, D.; Saha, T.; Talukdar, P. Chem. Commun. 2014, 50, 5510.
[35]
Yoo, M.; Park, S.; Kim, H.-J. RSC Adv. 2016, 6, 19910.
[36]
Dong, M.; Peng, Y.; Dong, Y.; Tang, N.; Wang, Y. Org. Lett. 2012, 14, 130.
[37]
Peng, Y.; Dong, Y. M.; Dong, M.; Wang, Y. W. J. Org. Chem. 2012, 77, 9072.
[38]
Hou, P.; Chen, S.; Wang, H.; Wang, J.; Voitchovsky, K.; Song, X. Chem. Commun. 2014, 50, 320.
[39]
Jiang, X. J.; Vieweger, M. C.; Bollinger, J. C.; Dragnea, B.; Lee, D. Org. Lett. 2007, 9, 3579.
[40]
Bao, Y.; Liu, B.; Wang, H.; Tian, J.; Bai, R. Chem. Commun. 2011, 47, 3957.
[41]
Goswami, S.; Das, A. K.; Manna, A.; Maity, A. K.; Fun, H.-K.; Quah, C. K.; Saha, P. Tetrahedron Lett. 2014, 55, 2633.
[42]
Liu, S.; Zhang, L.; Zhou, P.; Yang, Y.; Wu, W. Sens. Actuators, B 2018, 255, 401.
[43]
Zhang, X.; Shiraishi, Y.; Hirai, T. Tetrahedron Lett. 2007, 48, 8803.
[44]
Kanagaraj, K.; Pitchumani, K. Chem.-Asian J. 2014, 9, 146.
[45]
Leng, Y.; Zhang, J.; Li, Q.; Zhang, Y.; Lin, Q.; Yao, H.; Wei, T. Spectrochim. Acta, Part A 2016, 167, 116.
[46]
Yuan, X.; Zhao, C.; Lu, Y.; Shen, Y.; Wang, C. J. Photochem. Photobiol., A 2018, 361, 41.
[47]
Zhang, M.; Li, M.; Li, F.; Cheng, Y.; Zhang, J.; Yi, T.; Huang, C. Dyes Pigm. 2008, 77, 408.
[48]
Sarkar, A.; Bhattacharyya, S.; Mukherjee, A. Dalton Trans. 2016, 45, 1166.
[49]
Zhou, K.; Ren, M.; Wang, L.; Li, Z.; Lin, W. Spectrochim. Acta, Part A 2018, 204, 777.
[50]
Qu, Y.; Hua, J.; Tian, H. Org. Lett. 2010, 12, 3320.
[51]
Yang, H.; Song, H.; Zhu, Y.; Yang, S. Tetrahedron Lett. 2012, 53, 2026.
[52]
Chen, X.; Leng, T.; Wang, C.; Shen, Y.; Zhu, W. Dyes Pigm. 2017, 141, 299.
[53]
Li, D.; Tian, Z. J. Mol. Struct. 2020, 1206. 127631
[54]
Wu, N.; Zhao, L.; Jiang, C.; Li, P.; Liu, Y.; Fu, Y.; Ye, F. J. Mol. Liq. 2020, 302. 112549.
[55]
Ma, Y.; Li, G.; Jiang, T.; Zhang, X.; Zhang, F.; Xu, S. Arabian J. Chem. 2022, 15, 103940.
[56]
Kim, H. Y.; Im, H. G.; Chang, S.-K. Dyes Pigm. 2015, 112, 170.
[57]
Du, M.; Huo, B.; Liu, J.; Li, M.; Fang, L.; Yang, Y. Anal. Chim. Acta 2018, 1030, 172.
[58]
Li, L.; Zhang, M.; Ding, L.; Ren, G.; Hou, X.; Liu, W.; Wang, H.; Wang, B.; Yan, L.; Diao, H. Spectrochim. Acta, Part A 2021, 252, 119518.
Options
文章导航

/

〈 〉