Citation: Yingpeng ZHANG, Xingxing LI, Yunshang YANG, Zhidong TENG. A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine[J]. Chinese Journal of Inorganic Chemistry, ;2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064 shu

A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine

1.
School of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou 730050, China
2.
Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Lanzhou 730046, China

Corresponding author: Yingpeng ZHANG, yingpengzhang@126.com
Received Date: 25 February 2025
Revised Date: 24 April 2025

Figures(14)

A fluorescence quenching probe (THI) for visually detecting hydrazine (N₂H₄) was synthesized and characterized by Knoevenagel condensation reaction using pyrazole derivatives as fluorescent groups. Spectroscopic studies revealed that, under optimal excitation and emission wavelengths, the THI exhibited high selectivity and sensitivity toward N₂H₄, maintaining excellent anti-interference performance even in the presence of various analytes. Additionally, the THI demonstrated ultrafast response time (18 s), attributed to the efficient nucleophilic addition reaction between its optimized molecular recognition site and N₂H₄. The detection limit for N₂H₄ was determined to be 0.141 μmol·L^-1, meeting the requirements for trace-level analysis. The detection mechanism, verified by mass spectrometry and density functional theory calculations, is ascribed to N₂H₄-induced intramolecular charge transfer (ICT), leading to fluorescence quenching. Furthermore, THI was successfully fabricated into test strips for the quantitative detection of N₂H₄ and applied for fluorescence imaging of N₂H₄ in HeLa cells.
- hydrazine,
- pyrazole derivative,
- intramolecular charge transfer,
- visual detection,
- fluorescent probe
1. [1]
  WANG B B, HE W M, LI X L, ZHAO W, QIU H T, ZHANG H. Engineering a fluorescent probe for the visual and wearable detection of N₂H₄ in foods, environment samples and biological imaging[J]. Spectroc. Acta Pt. A‒Molec. Biomolec. Spectr., 2025, 327: 125365 doi: 10.1016/j.saa.2024.125365
2. [2]
  LI Y N, WU X M, YANG S X, LIANG S, TIAN H Y, SUN B G. A natural light visible colorimetric responses fluorescent probe for hydrazine detection[J]. Anal. Sci., 2020, 36(3): 323-327 doi: 10.2116/analsci.19P287
3. [3]
  TU L P. Study on the design, synthesis and properties of fluorescent probes for hydrazine and several anions[D]. Chengdu: Sichuan University, 2021: 3-4
4. [4]
  ZHU T, ZHU X J, NIU W F, YU Y, REN X, LIN J. Comparative study of domestic and foreign emission standards for volatile organic compounds[J]. Journal of Mining Science and Technology, 2020, 5(2): 209-218
5. [5]
  ZHANG M F, CHEN K, SUN J, GAO Z Z, HOU X F. A nanoparticle probe for detecting hydrazine and its bioimaging application[J]. Chemistry, 2021, 84(8): 835-840
6. [6]
  ZHANG S. Design, synthesis, and its application research of three small molecule fluorescent probes[D]. Lanzhou: Lanzhou University, 2023: 2-21
7. [7]
  LUO J, LIU B S, ZHANG Y C, WANG B K, GUO B B, SHE L, CHEN T H. Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution [J]. Chinese J. Inorg. Chem., 2024, 40(12): 2438-2444 doi: 10.11862/CJIC.20240240
8. [8]
  YAN J L, WU W N, WANG Y. A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application[J] Chinese J. Inorg. Chem., 2024, 40(9): 1653-1660 doi: 10.11862/CJIC.20240154
9. [9]
  ZHANG Y, JU Y, LÜ K D, CHEN W B, HU L Q, YI C L. Application of organic fluorescent probe in food safety detection[J]. Journal of Henan University of Technology (Natural Science Edition), 2023, 44(6): 132-141
10. [10]
  WANG Q, LIU Y L, WU L F, ZHANG W J, ZUO X L, YANG W D, WU C. Construction of a reaction-based fluorescent probe and its application in the detection of mercury ions in environmental water[J]. Environmental Chemistry, 2024, 43(4): 1392-1400
11. [11]
  WANG H L, ZHENG H, HUANG J X, HUANG W D, YANG L Y, LI W. A benzoxazole-based turn-on fluorescent probe for visual detection of N₂H₄[J]. Chinese J. Inorg. Chem., 2024, 40(2): 353-360 doi: 10.11862/CJIC.2023.189
12. [12]
  SUN X F, ZHU Y Y, XIE X H, SHENG X, WANG S X. Synthesis and properties of hydrazine fluorescent probe based on coumaryn schiff base[J]. Chemical Reagents, 2024, 46(10): 52-57
13. [13]
  FU D Q, WANG X D, LIU B. Old drug, new use: The thalidomide-based fluorescent probe for hydrazine detection[J]. Spectroc. Acta Pt. A‒Molec. Biomolec. Spectr., 2024, 309: 123808 doi: 10.1016/j.saa.2023.123808
14. [14]
  JU Z Y, SHU P H, XIE Z Y, JIANG Y Q, TAO W J, XU Z H. A flavone-based fluorescent probe for hydrazine and its bioimaging in live cells[J]. Chin. J. Org. Chem., 2019, 39(3): 697-702
15. [15]
  CIEPLAK A S. Stereochemistry of nucleophilic addition to cyclohexanone. The importance of two-electron stabilizing interactions[J]. J. Am. Chem. Soc., 2002, 103(15): 4540-4552
16. [16]
  LIU L, CHEN L, HU X L, ZHONG K L, ZHANG J L, TANG L J. Application and cell imaging of turn-on fluorescent probe for hydrogen sulfide based on benzopyran in food samples[J]. Chin. J. Org. Chem., 2024, 44(6): 2027-2032
17. [17]
  ZHANG Y P, YANG X, YANG F, YANG Y S, LI X X, ZHANG H R. Pyrazole probes for the detection of N₂H₄ with ICT properties in live cells and soils[J]. J. Mol. Struct., 2024, 1312: 138498 doi: 10.1016/j.molstruc.2024.138498
18. [18]
  YANG Z Q, LIU X K, JIANG L N, WANG M. Design, synthesis and application of fluorescence resonance energy transfer-based ratiometric hydrazine fluorescent probe[J]. Chin. J Org Chem., 2019, 39(5): 1483-1488
19. [19]
  HU Y R, ZHANG S L, LUO H Y, ZHAO L Y, GUO X D, WANG S Q, HU R, YANG G Q. Design and application of a novel chalcone derivative fluorescent probe for aminopeptidase N[J] Chinese J. Org. Chem., 2024, 44(7): 2257-2264
20. [20]
  HUANG C J, LIU B N, ZHANG S J, WANG P B, XU W R. Synthesis and pharm acological activity of pyrazol[J]. Chinese Journal of New Drugs, 2007, 16(24): 2043-2044
21. [21]
  LI X F. Synthesis and application of pyrazole-pyrazoline-based fluorescent probes[D]. Lanzhou: Lanzhou University of Technology, 2021: 28-39
22. [22]
  YANG Y S, ZHANG Z, ZHANG Y P, LIANG Y N, LI X X, TENG Z D. Synthesis and application of specific N₂H₄ fluorescent probes with AIE effect based on pyrazole structure[J]. J. Fluoresc., 2024, 19: 1-12
23. [23]
  LAI Q Q, SI S F, QIN T Y, LI B J, WU H X, LIU B, XU H H, ZHAO C. A novel red-emissive probe for colorimetric and ratiometric detection of hydrazine and its application in plant imaging[J]. Sens. Actuator B‒Chem., 2020, 307: 127640
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沈阳化工大学材料科学与工程学院沈阳 110142