ARTICLES

Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu2+ and Glyphosate

  • Mianyuan Wu ,
  • Yanchao Yu ,
  • Yang Liu ,
  • Jun You ,
  • Wenju Wu ,
  • Bo Liu
Expand
  • a Key Laboratory of Green Chemical Engineering and Technology of College of Heilongjiang Province, College of Materials Science and Chemical Engineering, Harbin University of Science and Technology, Harbin 150080
    b Institute of Petrochemistry, Heilongjiang Academy of Sciences, Harbin 150040
* Corresponding authors. E-mail: ;

Received date: 2021-09-29

  Revised date: 2021-10-28

  Online published: 2021-11-25

Supported by

National Natural Science Foundation of China(21908034); Natural Science Foundation of Heilongjiang Province(LH2021H001)

Abstract

A novel fluorescent probe L based on coumarin-derived acylhydrazone was designed and synthesized by using 7-(4-methoxyphenyl)ethynyl coumarin as report group. The probe L showed high selectivity and good anti-interference ability towards Cu2+ ion through the color of solution changed from light brown to yellow for naked-eye detection and significant fluorescence intensity quenched in the dimethyl sulfoxide (DMSO)/H2O [V:V=7:3, 2-[4-(2-hydroxyethyl)piperazin-1- yl]ethanesulfonic acid (HEPES) 10 mmol/L, pH=7.4] solution, and the detection limit of probe L to Cu2+ could reach 5.6×10–8 mol/L. Meanwhile, the L-Cu2+ system has high selectivity, good sensitivity, wide pH range (5~9) and low detection limit (11.3 ng/mL) for the detection of glyphosate by ligand replacement method. In addition, glyphosate detection was assessed within the actual water samples for testing the L-Cu2+actual application and the method was expected to the detection in environmental samples.

Cite this article

Mianyuan Wu , Yanchao Yu , Yang Liu , Jun You , Wenju Wu , Bo Liu . Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu2+ and Glyphosate[J]. Chinese Journal of Organic Chemistry, 2022 , 42(3) : 803 -811 . DOI: 10.6023/cjoc202109049

References

[1]
Elcin, S.; Deligoz, H.; Bhatti, A. A.; Oguz, M.; Karakurt, S.; Yilmaz, M. Sens. Actuators, B 2016, 234, 345.
[2]
Sunnapu, O.; Kotla, N. G.; Maddiboyina, B.; Marepally, S.; Shanmugapriya, J.; Sekar, K.; Singaravadivel, S.; Sivaraman, G. Anal. Chem. 2017, 2, 7654.
[3]
He, J. W.; Xie, Z. F.; Xue, S. S.; Liu, Y. C.; Shi, W.; Chen, X. Chin. J. Org. Chem. 2021, 41, 2839. (in Chinese)
[3]
(何佳伟, 解正峰, 薛松松, 刘宇程, 石伟, 陈鑫, 有机化学, 2021, 41, 2839.)
[4]
Viles, J. H. Coord. Chem. Rev. 2012, 256, 2271.
[5]
Fasea, K. D.; Abolaji, A. O.; Faloye, T. R.; Odunsi, A. Y.; Oyetayo, B. O.; Enya, J. I.; Rotimi, J. A.; Akinyemi, R. O.; Whitworth, A. J.; Aschner, M. J. Trace Elem. Med. Biol. 2021, 67, 126779.
[6]
Mezzaroba, L.; Alfieri, D. F.; Simao, A. C.; Reiche, E. M. Neurotoxichology 2019, 74, 230.
[7]
Keep, K. P.; Squitti, R. Coord. Chem. Rev. 2019, 397, 168.
[8]
Lei, M. M.; Zhou, Q. H.; Yang, L.; Xu, Z. H.; Yang, F. L. Chin. J. Org. Chem. 2020, 40, 2798. (in Chinese)
[8]
(雷萌萌, 周起航, 杨莉, 许志红, 杨凤岭, 有机化学, 2020, 40, 2798.)
[9]
Fang, R.; Ding, X.; Luo, W.; Hong, C. Chin. J. Org. Chem. 2020, 40, 2949. (in Chinese)
[9]
(房茹, 丁旭, 罗稳, 洪琛, 有机化学, 2020, 40, 2949.)
[10]
Beckie, H. J.; Flower, K. C.; Ashworth, M. B. Plants 2020, 9, 96.
[11]
Heymann, A. K.; Schnabel, K.; Billenkamp, F.; Bühler, S.; Frahm, J.; Kersten, S.; Hüther, L.; Meyer, U.; Soosten, D. V.; Trakooljul, N.; Teifke, J. P.; Dänicke, S. Plos One 2021, 16, e0246679.
[12]
Tu, Q.; Yang, T. X.; Qu, Y. Q.; Gao, S. Y.; Zhang, Z. Y.; Zhang, Q. M.; Wang, Y. L.; Wang, J. Y.; He, L. L. Analyst 2019, 144, 2017.
[13]
Cao, Y.; Wang, L. N.; Shen, C.; Wang, C. Y.; Hu, X. Y.; Wang, G. X. Sens. Actuators, B 2019, 283, 487.
[14]
Aguirre, M. C.; Urreta, S. E.; Gomez, C. G. Sens. Actuators, B 2019, 284, 675.
[15]
Gandhi, K.; Khan, S.; Patrikar, M.; Markad, A.; Kumar, N.; Choudhari, A.; Sagar, P.; Indurkar, S. Environ. Challenges 2021, 4, 100149.
[16]
Mesnage, R.; Defarge, N.; Vendomis, J. S.; Seralini, G. E. Food Chem. Toxicol. 2015, 84, 133.
[17]
Benedetti, A. L.; Vituri, C. L.; Trentin, A. G.; Dominues, M. A.; Silva, M. A. Toxicol. Lett. 2004, 153, 227.
[18]
Jasper, R.; Locatelli, G. O.; Pilati, C.; Locatelli, C. Interdiscip. Toxicol. 2012, 5, 133.
[19]
Mesnage, R.; Biserni, M.; Wozniak, E.; Xenakis, T.; Mein, C. A.; Antoniou, M. N. Toxicol. Rep. 2018, 5, 819.
[20]
Topal, A.; Atamanalp, M.; Ucar, A.; Oruc, E.; Kocaman, E. M.; Sulukan, E.; Akdemir, F.; Beydemir, S.; Kilinc, N.; Erdogan, O.; Ceyhun, S. B. Ecotoxicol. Environ. Saf. 2015, 111, 206.
[21]
Schnabel, K.; Schmitz, R.; Frahm, J.; Meyer, U.; Breves, G.; Danicke, S. Arch. Anim. Nutr. 2020, 74, 1.
[22]
Guyton, K. Z.; Loomis, D.; Grosse, Y.; Ghissassi, F. E.; Tallaa, L. B.; Guha, N.; Scoccianti, C.; Mattock, H.; Straif, K. Lancet Oncol. 2015, 16, 490.
[23]
Tseng, S. H.; Lo, Y. W.; Chang, P. C.; Chou, S. S.; Chang, H. M. J. Agric. Food Chem. 2004, 52, 4057.
[24]
Wang, S.; Liu, B. M.; Yuan, D. X.; Ma, J. Talanta 2016, 161, 700.
[25]
Liao, Y.; Berthion, J. M.; Colet, I.; Merlo, M.; Nougadere, A.; Hu, R. J. Chromatogr. A 2018, 1549, 31.
[26]
Wumbei, A.; Goeteyn, L.; Lopez, E.; Houbraken, M.; Spanoghe, P. Food Addit. Contam., art B 2019, 12, 231.
[27]
Gendy, K. E.; Mosallam, E.; Ahmed, N.; Aly, N. Anal. Biochem. 2018, 557, 1.
[28]
Wang, L.; Bi, Y. D.; Li, Y. J.; Ding, H.; Ding, L. RSC Adv. 2016, 6, 85820.
[29]
Gui, M. F.; Jiang, J.; Wang, X.; Yan, Y. X.; Li, S. Q.; Xiao, X. L.; Liu, T. B.; Liu, T. G.; Feng, Y. Sens. Actuators, B 2017, 243, 696.
[30]
Wang, X. F.; Sakinati, M.; Yang, Y. X.; Ma, Y.; Yang, M.; Luo, H. B.; Hou, C. J. Anal. Methods 2020, 12, 520.
[31]
Gou, Z. N.; Zhao, S. S.; Zhang, P. Chin. J. Synth. Chem. 2019, 27, 673. (in Chinese)
[31]
(苟珍妮, 赵顺省, 张盼, 合成化学, 2019, 27, 673.)
[32]
Zhong, K. L.; Guo, B. F.; Sun, X. H.; Zhou, X.; Zhang, Q.; Tang, L. J.; Zhang, X. R. Chin. J. Org. Chem. 2017, 37, 2002. (in Chinese)
[32]
(钟克利, 郭宝峰, 孙笑寒, 周雪, 张强, 汤立军, 张行荣, 有机化学, 2017, 37, 2002.)
[33]
Shi, F.; Gui, S. Q.; Liu, H. L.; Pu, S. Z. Dyes Pigm. 2020, 173, 107914.
[34]
Tang, Y.; Li, Y. Y.; Han, J.; Mao, Y. L.; Ni, L.; Wang, Y. Spectrochim. Acta, Part A 2019, 208, 299.
[35]
He, G. J.; Liu, X. L.; Xu, J. H.; Yang, L. L.; Fan, A. Y.; Wang, S. J.; Wang, Q. Z. Spectrochim. Acta, Part A 2018, 190, 116.
[36]
Paul, K.; Bindal, S.; Luxami, V. Bioorg. Med. Chem. Lett. 2013, 23, 3667.
[37]
Yin, H. J.; Zhang, B. C.; Yu, H. Z.; Zhu, L.; Feng, Y.; Zhu, M. Z.; Guo, Q. X.; Meng, X. M. J. Org. Chem. 2015, 80, 4306.
Outlines

/