Citation: Hanlin WANG, Han ZHENG, Jiexun HUANG, Weidong HUANG, Longyuan YANG, Wu LI. A Benzoxazole-based turn-on fluorescent probe for visual detection of N₂H₄[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(2): 353-360. doi: 10.11862/CJIC.2023.189 shu

A Benzoxazole-based turn-on fluorescent probe for visual detection of N₂H₄

Hanlin WANG ^{1, 2,,} ,
Han ZHENG ^{1, 2} ,
Jiexun HUANG ^{1, 2} ,
Weidong HUANG ³ ,
Longyuan YANG ^{1, 2} ,
Wu LI ^{1, 2}

1.
School of Environmental Seience and Engineering, Hubei Polytechnic University, Huangshi, Hubei 435003, China
2.
Hubei Key Laboratory of Mine Environmental Pollution Control & Remediation, Huangshi, Hubei 435003, China
3.
College of Chemistry and Chemical Engineering, Hubei Polytechnic University, Huangshi, Hubei 435003, China

Corresponding author: Hanlin WANG, whl2022hbpu@163.com
Received Date: 18 June 2023
Revised Date: 28 September 2023

Figures(13)

A turn-on fluorescent probe (HL2) for visual detection of N₂H₄ was synthesized and characterized using benzoxazole as a fluorophore, and its spectral properties were investigated. The experimental results indicated that HL2 had high selectivity and sensitivity to N₂H₄, strong anti-interference ability, and a wide pH response range (5-10). HL2 quickly recognized N₂H₄ within 2 min, accompanied by a color change of the probe solution from colorless to blue. The fluorescent intensity of HL2 showed excellent linear relationship with the concentration of N₂H₄ (0.1-25 μmol·L^-1), and its detection limit was evaluated to be 0.072 μmol·L^-1. In addition, HL2 can be applied to detecting N₂H₄ in real water samples, and it could also realize fluorescence imaging of N₂H₄ in HeLa cells.
- benzoxazole,
- fluorescent probe,
- hydrazine,
- visual detection,
- fluorescent imaging
1. [1]
  Zhang X Y, Yang Y S, Wang W, Jiao Q C, Zhu H L. Fluorescent sensors for the detection of hydrazine in environmental and biological systems: Recent advances and future prospects[J]. Coord. Chem. Rev., 2020,417213367. doi: 10.1016/j.ccr.2020.213367
2. [2]
  Popiotek L. Hydrazide-hydrazones as potential antimicrobial agents: Overview of the literature since 2010[J]. Med. Chem. Res., 2017,26:287-301. doi: 10.1007/s00044-016-1756-y
3. [3]
  ZHANG Y, LIU J F, YI R H, AI S F, CHENG H R, JIA W Z. Synthesis and application of a flavone-based fluorescent probe for detection of hydrazine[J]. Chin. J. Anal. Chem., 2018,46(4):511-516.
4. [4]
  Kao Y H, Chong C H, Ng W T, Lim D. Hydrazine inhalation hepatotoxicity[J]. Occup. Med., 2007,57:535-537. doi: 10.1093/occmed/kqm077
5. [5]
  Leakakos T, Shank R C. Hydrazine genotoxicity in the neonatal rat[J]. Toxicol. Appl. Pharmacol., 1994,126:295-300. doi: 10.1006/taap.1994.1119
6. [6]
  Zelnick S D, Mattie D R, Stepaniak P C. Occupational exposure to hydrazines: Treatment of acute central nervous system toxicity[J]. Aviat. Space Environ. Med., 2003,74:1285-1291.
7. [7]
  Biswajit R, Subhajit B. The design strategies and mechanisms of fluorogenic and chromogenic probes for the detection of hydrazine[J]. Anal. Methods, 2018,10:1117-1139. doi: 10.1039/C7AY02866K
8. [8]
  Huang Y F, Liang J P, Fan Z F. A review: Small organic molecule dual/multi-organelle-targeted fluorescent probes[J]. Talanta, 2023,259124529. doi: 10.1016/j.talanta.2023.124529
9. [9]
  Chowdhury S, Rooj B, Dutta A, Mandal U. Review on recent advances in metal ions sensing using different fluorescent probes[J]. J. Fluoresc., 2018,28:999-1021. doi: 10.1007/s10895-018-2263-y
10. [10]
  CHEN X, LI S Y, WANG Y, WU W N, CHEN Z. A Schiff base fluorescent probe for Al³⁺: Synthesis and application in living cells imaging[J]. Chinese J. Inorg. Chem., 2022,38(10):1993-1998. doi: 10.11862/CJIC.2022.190
11. [11]
  Duan N, Wang H, Li Y, Yang S X, Tian H Y, Sun B G. The research progress of organic fluorescent probe applied in food and drinking water detection[J]. Coord. Chem. Rev., 2021,427213557. doi: 10.1016/j.ccr.2020.213557
12. [12]
  Choi M G, Hwang J, Moon J O, Sung J, Chang S K. Hdrazine-selective chromogenic and fluorogenic probe based on levulinated coumarin[J]. Org. Lett., 2011,13:5260-5263. doi: 10.1021/ol202136q
13. [13]
  Wang E F, Ma H L, Lu J X, Wang F Y, Ren J. Recent progress in the fluorescent probes for hydrazine detection[J]. Tetrahedron, 2022,124132989. doi: 10.1016/j.tet.2022.132989
14. [14]
  Yan L Q, Zhang S Q, Xie Y, Mu X Y, Zhu J B. Recent progress in the development of fluorescent probes for the detection of hydrazine (N₂H₄)[J]. Crit. Rev. Anal. Chem., 2020,52:210-229.
15. [15]
  Nguyen K H, Hao Y Q, Chen W S, Zhang Y T, Xu M T, Yang M H, Liu Y N. Recent progress in the development of fluorescent probes for hydrazine[J]. Luminescence, 2018,33:816-836. doi: 10.1002/bio.3505
16. [16]
  Chen M L, Lv X, Liu Y L, Zhao Y, Liu J, Wang P, Guo W. An 2-(2'-aminophenyl) benzoxazole-based OFF-ON fluorescent chemosensor for Zn²⁺ in aqueous solution[J]. Org. Biomol. Chem., 2011,9:2345-2349. doi: 10.1039/c0ob00983k
17. [17]
  Liu Y M, Fei Q, Shan H Y, Cui M H, Liu Q, Feng G D, Huan Y F. A novel fluorescent 'off-on-off' probe for relay recognition of Zn²⁺ and Cu²⁺ derived from N, N-bis(2-pyridylmethyl)amine[J]. Analyst, 2014,139:1868-1875. doi: 10.1039/c3an02230g
18. [18]
  Song Y, Zhou L Y, Wang J J, Wang F F, Yang Q B. Synthesis and application of benzoxazole derivative-based fluorescent probes for naked eye recognition[J]. Luminescence, 2020,35:1010-1016. doi: 10.1002/bio.3806
19. [19]
  Sheldrick G M. Crystal structure refinement with SHELXL[J]. Acta Crystallogr. Sect. C, 2015,C71:3-8.
20. [20]
  Cui L, Peng Z X, Ji C F, Huang J H, Huang D T, Ma J, Zhang S P, Qian X H, Xu Y F. Hydrazine detection in the gas state and aqueous solution based on the Gabriel mechanism and its imaging in living cells[J]. Chem. Commun., 2014,50:1485-1487. doi: 10.1039/C3CC48304E
21. [21]
  Wang L, Liu F Y, Liu H Y, Dong Y S, Liu T Q, Liu J F, Yao Y W, Wan X J. A novel pyrazoline-based fluorescent probe for detection of hydrazine in aqueous solution and gas state and its imaging in living cells[J]. Sensor. Actuat. B: Chem., 2016,229:441-452. doi: 10.1016/j.snb.2016.02.001
1. [1]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
2. [2]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
3. [3]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
4. [4]
  Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049
5. [5]
  Xin Lv , Hongxing Zhang , Kaibo Duan , Wenhui Dai , Zhihui Wen , Wei Guo , Junsheng Hao . Lighting the Way Against Cancer: Photodynamic Therapy. University Chemistry, 2024, 39(5): 70-79. doi: 10.3866/PKU.DXHX202309090
6. [6]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
7. [7]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
8. [8]
  Zijuan LI , Xuan LÜ , Jiaojiao CHEN , Haiyang ZHAO , Shuo SUN , Zhiwu ZHANG , Jianlong ZHANG , Yanling MA , Jie LI , Zixian FENG , Jiahui LIU . Synthesis of visual fluorescence emission CdSe nanocrystals based on ligand regulation. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 308-320. doi: 10.11862/CJIC.20240138
9. [9]
  Yue WANG , Zhizhi GU , Jingyi DONG , Jie ZHU , Cunguang LIU , Guohan LI , Meichen LU , Jian HAN , Shengnan CAO , Wei WANG . Effects of kelp-derived carbon dots on embryonic development of zebrafish. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1209-1217. doi: 10.11862/CJIC.20230423
10. [10]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
11. [11]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
12. [12]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
13. [13]
  Qin Hou , Jiayi Hou , Aiju Shi , Xingliang Xu , Yuanhong Zhang , Yijing Li , Juying Hou , Yanfang Wang . Preparation of Cuprous Iodide Coordination Polymer and Fluorescent Detection of Nitrite: A Comprehensive Chemical Design Experiment. University Chemistry, 2024, 39(8): 221-229. doi: 10.3866/PKU.DXHX202312056
14. [14]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
15. [15]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
16. [16]
  Yanxin Wang , Hongjuan Wang , Yuren Shi , Yunxia Yang . Application of Python for Visualizing in Structural Chemistry Teaching. University Chemistry, 2024, 39(3): 108-117. doi: 10.3866/PKU.DXHX202306005
17. [17]
  Ruming Yuan , Laiying Zhang , Xiaoming Xu , Pingping Wu , Gang Fu . Application of Mathematica in Visualizing Physical Chemistry Formulas. University Chemistry, 2024, 39(8): 375-382. doi: 10.3866/PKU.DXHX202401030
18. [18]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
19. [19]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
20. [20]
  Xinyu Liu , Weiran Hu , Zhengkai Li , Wei Ji , Xiao Ni . Algin Lab: Surging Luminescent Sea. University Chemistry, 2024, 39(5): 396-404. doi: 10.3866/PKU.DXHX202312021

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(592)
HTML views(52)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

A Benzoxazole-based turn-on fluorescent probe for visual detection of N2H4

Metrics

通讯作者: 陈斌, bchen63@163.com

A Benzoxazole-based turn-on fluorescent probe for visual detection of N₂H₄