Citation: LIU Yang, WU Mian-Yuan, YOU Jun, WU Wen-Ju, YU Yan-Chao. Synthesis and Application of Naphthalimide Schiff Base Fluorescent Probe for Detection of Copper Ion and Glyphosate[J]. Chinese Journal of Analytical Chemistry, ;2022, 50(5): 772-780. doi: 10.19756/j.issn.0253-3820.210829 shu

Synthesis and Application of Naphthalimide Schiff Base Fluorescent Probe for Detection of Copper Ion and Glyphosate

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, China

Corresponding author: YU Yan-Chao, yychao136@163.com
Received Date: 6 November 2021
Revised Date: 7 February 2022

Fund Project: Supported by the the National Natural Science Foundation of China (No.21908034) and the Natural Science Foundation of Heilongjiang Province, China (No.LH2021H001).

A naphthalimide Schiff base fluorescent probe L was designed and synthesized with 4-bromo-1,8-naphthalene dicarboxylic anhydride as raw material. Its structure was characterized by ¹H nuclear magnetic resonance (NMR),¹³C NMR, infrared (IR) spectroscopy and high resolution mass spectrometry (HRMS). In the CH₃CN-H₂O (75:25, V/V, 20 mmol/L HEPES, pH=7.4) solution, the probe possessed good selectivity and sensitivity to Cu²⁺ and with a detection limit as low as 0.37 μmol/L. The stoichiometric ratio of L to Cu²⁺ was 1:1, and the complex L-Cu²⁺ had high selectivity, good sensitivity, low detection limit of 0.56 μmol/L (0.09 μg/mL) and naked eye recognition for detection of glyphosate by ligand replacement menthod. In addition, the L-Cu²⁺ was succesfully used in detection of glyphosate in actual water samples, which indicated that the proposed probe had potential application in the field of environmental detection.
- Fluorescent probe,
- Schiff base,
- Naphthalimide,
- Copper ion,
- Glyphosate
1. [1]
2. [2]
  YIN K, WU Y X, WANG S S, CHEN L X. Sens. Actuators, B, 2016, 232:257-263.
3. [3]
  GAO W D, LI H, PU S J. Photochem. Photobiol., A, 2018, 364:208-218.
4. [4]
  ZHANG Z Y, LIU Y P, WANG E J. Dyes Pigm., 2019, 163:533-537.
5. [5]
  NASOMPHAN W, TANGBORIBOONRAT P, SMANMOO S. J. Fluoresc., 2017, 27(6):2201-2012.
6. [6]
  TANG L J, ZHOU P, ZHANG Q, HUANG Z L, ZHAO J, CAI M J. Inorg. Chem. Commun., 2013, 36:100-104.
7. [7]
  ZHANG Z Y, LIU Y P, WANG E J. Dyes Pigm., 2019, 163:533-537.
8. [8]
9. [9]
  LEE E A, ZIMMERMAN L R, BHULLAR B S, THURMAN E M. Anal. Chem., 2002, 74(19):4937-4943.
10. [10]
  HUHN C. Anal. Bioanal. Chem., 2018, 410:3041-3045.
11. [11]
  WANG S, LIU B M, YUAN D X, MA J. Talanta, 2016, 161:700-706.
12. [12]
  WANG L, BI Y D, GAO J, LI Y J, DING H, DING L. RSC Adv., 2016, 6:85820-85828.
13. [13]
  AGUIRRE M C, URRETA S E, GOMEZ C G. Sens. Actuators, B, 2019, 284:675-683.
14. [14]
  CORBERA M, HIDALGO M, SALVADO V, WIECZOREK P P. Anal. Chim. Acta, 2005, 540(1):3-7.
15. [15]
  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(5):490-491.
16. [16]
  BENEDETTI A L, VITURI C L, TRENTIN A G, DOMINGUES M A C, ALVAREZ-SILVA M. Toxicol. Lett., 2004, 153(2):227-232.
17. [17]
  MESNAGE R, BISERNI M, WOZNIAK E, XENAKIS T, MEIN C A, ANTONIOU M N. Toxicol. Rep., 2018, 5:819-826.
18. [18]
  GUO J J, ZHANG Y, LUO Y L, SHEN F, SUN C Y. Talanta, 2014, 125(11):385-392.
19. [19]
  HSU C C, WHANG C W. J. Chromatogr. A, 2009, 1216:8575-8680.
20. [20]
  SUN Y J, WANG C Y, WEN Q Y, WANG G X, WANG H H, QU Q S, HU X Y. Chromatographia, 2010, 72:679-686.
21. [21]
22. [22]
23. [23]
  ZHANG J, ZHAO B J, LI C, ZHU X F, QIAO R Z. Sens. Actuators, B, 2016, 196:117-122.
24. [24]
  NI H Z, WANG Q M, JIN L, WANG W L, DAI L H, ZHAO C. J. Lumin., 2019, 206:125-131.
25. [25]
26. [26]
  WANG X F, SAKINATI M, YANG Y X, MA Y, YANG M, LUO H B, HOU C J, HOU D Q. Anal. Methods, 2020, 12:520-527.
27. [27]
  WANG D, LIN B X, CAO Y J, GUO M L, YU Y. J. Agric. Food Chem., 2016, 64:6042-6050.
28. [28]
  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, 243:696-703.
29. [29]
  MOTEKAITIS R J, MARTELL A E. J. Coord. Chem., 1985, 14:139-149.
30. [30]
  SHEALS J, GRANSTROM M, SJOBERG S, PERSSON P. J. Colloid Sci., 2003, 262:38-47.
31. [31]
  MUSHTAQ N, CHEN G F, SIDRA L R, FANG X Z. RSC Adv., 2016, 6(30):25302-25310.
32. [32]
  SHI F, CUI S Q, LIU H L, PU S Z. Dyes Pigm. 2020, 173:107914.
33. [33]
  TANG Y, LI Y Y, HAN J, MAO Y L, NI L, WANG Y. Spectrochim. Acta, Part A, 2019, 208:299-308.
34. [34]
  SHEALS J, PERSSON P, HEDMAN B. Inorg. Chem., 2001, 40(17):4302-4309.
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