Citation: ZOU Ying-yi, FENG Rui-hong, LUO Ying-xin, MA Ming-jun, ZHU Lu-yao, MA Li-jun. Study on Salicylaldehyde Derivatives Modified by Naphthalene Isothiocyanate as Fluorescent Probe for Fluoride Ion[J]. Chinese Journal of Analytical Chemistry, ;2022, 50(4): 574-584. doi: 10.19756/j.issn.0253-3820.210878 shu

Study on Salicylaldehyde Derivatives Modified by Naphthalene Isothiocyanate as Fluorescent Probe for Fluoride Ion

School of Chemistry, South China Normal University, Guangzhou 510006, China

Corresponding author: MA Li-jun, mlj898021@scnu.edu.cn
Received Date: 6 December 2021
Revised Date: 7 March 2022

Fund Project: Supported by the Natural Science Foundation of Guangdong Province,China(No. 2015A030313392)the Science and Technology Planning Project of Guangzhou,China(NO. 2018J2200342)

Two fluorescent molecules(1 and 2) were synthesized by salicylaldehyde and 4-(diethylamino) salicylaldehyde with naphthalene isothiocyanate.Their structures were characterized by nuclear magnetic resonance(NMR) and mass spectrometry(MS).The results of UV-vis absorption spectra and fluorescence spectra showed that molecule 1 and molecule 2 had high sensitivity to fluoride ion(F^-) in DMSO solution, which could be used as fluorescence probes for F^- detection.Probe 1(molecule 1) showed fluorescence enhancement to F^-, and the fluorescence intensity increased by 15 times when F^-concentration was 20.0μmol/L.Compared to probe 1, probe 2(molecule 2) showed high selectivity ratio fluorescence recognition for F^- due to the presence of diethylamino group.The addition of F^-could cause decrease of fluorescence emission peak of probe 2 at 456 nm, while a new fluorescence emission peak appeared at 503 nm and gradually increased.Probes 1 and 2 had low detection limits of 0.35μmol/L and 0.68μmol/L toward F^-respectively.By the B-H equation, the constants of probe 1 and probe 2 to F^- were 3.8×10⁴ L/mol and 6.98×10³ L/mol, indicating that the two probes had strong binding affinity with F^-.In addition, the binding modes between probe 1 and probe 2 and F^-were investigated by ¹H NMR.The analysis of experimental results showed that the fluorescence recognition mechanism of both two probes was intramolecular charge transfer(ICT).Finally, the test papers prepared by the two probes were used for simple fluorescence detection of F^- in toothpaste solution, which proved their good practicability.
- Fluorescent probe,
- Naphthalene isothiocyanate,
- Salicylaldehyde,
- Fluoride ion,
- Intramolecular charge transfer
1. [1]
  ZHOU Y, ZHANG J F, YOON J Y. Chem. Rev., 2014, 114(10):5511-5571.
2. [2]
  ROCHA R A, ROJAS D, CLEMENTE M J, RUIZ A, DEVESA V, VELEZ D. J. Agric. Food Chem., 2013, 61(45):10708-10713.
3. [3]
  JIA B, ZONG L, LEE J Y, LEI J, ZHU Y, XIE H, JULIA L C, MIA C F, NA Q, DONG J, MICHAEL W M,KIMBERLY J B, IRINA B. Sci. Rep., 2019, 9:2575.
4. [4]
  SHAO F Q, ZHANG S M, QI C, WANG Y, CHEN Y. Clin. Nucl. Med., 2017, 42(9):711-713.
5. [5]
  MOHAMMADI A A, YOUSEFI M, YASERI M, JALILZADEH M, MAHVI A H. Sci. Rep., 2017, 7:17300.
6. [6]
  YADAV K K, KUMAR S, PHAM Q B, GUPTA N, REZANIAE S, KAMYAB H, YADAV S, VYMAZAL J,KUMAR V, TRI D Q, TALAIEKHOZANI A, PRASAD S, REECE L M, SINGH N, MSURYA P K, CHO J.Ecotoxicol. Environ. Saf., 2019, 182:109362.
7. [7]
8. [8]
  RICHARD A N, BEKELCHA T G, HERN K. New J. Chem., 2018, 42:12263.
9. [9]
  IBBA F, PUPO G, THOMPSON A L, BROWN J M, CLARIDGE T D W, GOUVERNEUR V. J. Am. Chem. Soc.,2020, 142(46):19731-19744.
10. [10]
  SHAW W M. Anal. Chem., 1954, 26(7):1212-1214.
11. [11]
  MICHALSKI R. J. Food Qual., 2006, 29(6):607-616.
12. [12]
  CHEN G J, PENG C Y, FANG J Y, DONG Y Y, ZHU X H, CAI H M. Desalin. Water Treat., 2016, 57(26):12385-12395.
13. [13]
  DU M, HUO B L, LIU J M, LI M W, FANG L Q, YANG Y X. Anal. Chim. Acta, 2018, 1030:172-182.
14. [14]
  LIU J B, WANG W H, LI G D, WANG R X, LEUNG C H, MA D L. ACS Omega, 2017, 2(12):9150-9155.
15. [15]
  ZHENG H Y, LIAN X, QIN S J, YAN B. ACS Omega, 2018, 3(10):12513-12519.
16. [16]
  LONG L L, HUANG M Y, WANG N, WU Y J, WANG K, GONG A H, ZHANG Z J. SESSLER J L. J. Am. Chem.Soc., 2018, 140(5):1870-1875.
17. [17]
  LI W, GONG X Y, FAN X P, YIN S L, SU D D, ZHANG X B, YUAN L. Chin. Chem. Lett., 2019, 30(10):1775-1790.
18. [18]
  HE X J, XIONG W, ZHANG L L, XU C C, FAN J Y, QIAN Y, WEN J S, DING F, SHEN J L. Dyes Pigm., 2020,174:108059.
19. [19]
  CHEN S Y, YU H, ZHAO C, HU R, ZHU J, LI L. Sens. Actuators, B, 2017, 250:591-600.
20. [20]
  ZHANG P S, WANG H, HONG Y X, YU M L, ZENG R J, LONG Y F, CHEN J. Biosens. Bioelectron., 2018, 99:318-324.
21. [21]
  SHEN Y M, ZHANG X Y, ZHANG Y Y, LI H T, CHEN Y D. Sens. Actuators, B, 2018, 258:544-549.
22. [22]
  WU X M, WANG H, YANG S X, TIAN H Y, LIU Y G, SUN B G. ACS Omega, 2019, 4(3):4918-4926.
23. [23]
24. [24]
25. [25]
  SHARMA S, HUNDAL M S, HUNDAL G. Tetrahedron Lett., 2013, 54(19):2423-2427.
26. [26]
  NA Y J, CHOI Y W, YUN J Y, PARK K M, CHANG P S, KIM C. Spectrochim. Acta, Part A, 2015, 136(C):1649-1657.
27. [27]
  SARAVANA L A K, RAMALINGAM T, MPPRTHY S K, ANANDRAM S. Ind. Eng. Chem. Res., 2011, 50(22):12379-12383.
28. [28]
  YAN G T, LI H, ZHU Y R, SHI B B, QU W J, LIN Q, YAO H, ZHANG Y M, WEI T B. New J. Chem., 2015,39(11):8797-8801.
29. [29]
  JU B C, DONGJU Y, HANGYUL L, HYOJIN L, KI T K, CHEAL K. ACS Omega, 2019, 4(7):12537-12543.
30. [30]
  BENESI H A,HILDEBRAND J H. J. Am. Chem. Soc., 1949, 71:2703-2707.
31. [31]
  QIU S Y, CUI S Q, SHI F, PU S Z. ACS Omega, 2019, 4(12):14841-14848.
32. [32]
  YUAN X, XU X J, ZHAO C X, ZHANG F, LU Y X, SHEN Y J, WANG C Y. Sens. Actuators, B, 2017, 253:1096-1105.
33. [33]
  SU H Y, HUANG W W, YANG Z Y, LIN H, LIN H K. J. Inclusion Phenom. Macrocyclic Chem., 2012, 72(1):221-225.
34. [34]
  KUMAR D, THOMAS K R J. RSC Adv., 2014, 4(99):56466-56474.
35. [35]
  MAHAPATRA A K, MAITI K, SAHOO P, NANDI P K. J. Lumin., 2013, 143:349-354.
36. [36]
  WANG Y, ZHAO Q, ZANG L B, LIANG C S, JIANG S M. Dyes Pigm., 2015, 123:166-175.
37. [37]
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