Citation: WANG Ning, ZHOU Dongxue, YANG Jinchuang, AN Yue, LYU Chengwei. Determination of Hydrogen Sulfide in Water by Biphenyl Ratio Fluorescence Probe[J]. Chinese Journal of Applied Chemistry, ;2017, 34(4): 449-455. doi: 10.11944/j.issn.1000-0518.2017.04.160301 shu

Determination of Hydrogen Sulfide in Water by Biphenyl Ratio Fluorescence Probe

College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China

Corresponding author: AN Yue, anyue_11@163.com LYU Chengwei, chengweilv@126.com
Received Date: 28 July 2016
Revised Date: 9 October 2016
Accepted Date: 9 November 2016

Fund Project: the Higher Education Research Program of Education Department of Liaoning Province of China L2014421the National Natural Science Foundation of China 21403100

Figures(8)

A biphenyl-derived ratiometric fluorescent probe (WN) for the detection of H₂S was synthesized using 4, 4'-biphenyl dicarboxylic acid as the raw material and characterized by ¹H NMR, ¹³C NMR, and MS. For the purpose of detection of H₂S in aqueous solution, its fluorescent properties had been systematically researched. The results show that probe WN exhibits good sensitivity and selectivity for detection of H₂S, response time is 12 min. WN has strong anti-interference ability to biological mercaptan (Cys, Gsh), active oxides (H₂O₂, ClO^-), various anions and cations (H₂PO₄^-, SO₄^2-, Cl^-, HCO₃^-, CO₃^2-, Mg²⁺, Zn²⁺, K⁺, Ca²⁺, Na⁺), and a good fluorescence response in a wide pH range, the fluorescence in tensity has good linear relation ships with H₂S in the range of 1.1~350 μmol/L (R²=0.9943), the detection limit of H₂S is estimated to be 1.07×10^-6 mol/L. The test for three different water samples shows that the probe WN has a certain application significance in the detection of H₂S in water.
- hydrogen sulfide,
- azide group,
- ratiometric fluorescent probe
1. [1]
  Riesch R, Plath M, Schlupp I. Colonisation of Toxic Environments Drives Predictable Life-History Evolution in Livebearing Fishes (Poeciliidae)[J]. Ecol Lett, 2014,17(1):65-71. doi: 10.1111/ele.2013.17.issue-1
2. [2]
  LI Haijian. Reasons and Countermeasures of Hydrogen Sulfide in Water[J]. Sci Fish Farm, 2002(10)34.
3. [3]
  Hou P, Li H, Chen S. A Highly Selective and Sensitive 3-Hydroxyflavone-based Colorimetric and Fluorescent Probe for Hydrogen Sulfide with a Large Stokes Shift[J]. Tetrahedron, 2016,72(24):3531-3534. doi: 10.1016/j.tet.2016.04.079
4. [4]
  Yang Y, Lei Y, Zhang X. A Ratiometric Strategy to Detect Hydrogen Sulfide with a Gold Nanoclusters Based Fluorescent Probe[J]. Talanta, 2016,154:190-196. doi: 10.1016/j.talanta.2016.03.066
5. [5]
  Hu L F, Lu M, Wu Z Y. Hydrogen Sulfide Inhibits Rotenone-induced Apoptosis via Preservation of Mitochondrial Function[J]. Mol Pharmacol, 2009,75(1):27-34. doi: 10.1124/mol.108.047985
6. [6]
  Kulkarni K H, Monjok E M, Zeyssig R. Effect of Hydrogen Sulfide on Sympathetic Neurotransmission and Catecholamine Levels in Isolated Porcine Iris-Ciliary Body[J]. Neurochem Res, 2009,34(3):400-406. doi: 10.1007/s11064-008-9793-7
7. [7]
  Kimura H. Hydrogen Sulfide:Its Production, Release and Functions[J]. Amino Acids, 2011,41(1):113-121. doi: 10.1007/s00726-010-0510-x
8. [8]
  Schiavon G, Zotti G, Toniolo R. Electrochemical Detection of Trace Hydrogen Sulfide in Gaseous Samples by Porous Silver Electrodes Supported on Ion-Exchange Membranes (Solid Polymer Electrolytes)[J]. Anal Chem, 1995,67(2):318-323. doi: 10.1021/ac00098a015
9. [9]
  Guenther E A, Johnson K S, Coale K H. Direct Ultraviolet Spectrophotometric Determination of Total Sulfide and Iodide in Natural Waters[J]. Anal Chem, 2001,73(14):3481-3487. doi: 10.1021/ac0013812
10. [10]
  Kass M, Ivaska A. Spectrophotometric Determination of Sulphur Dioxide and Hydrogen Sulphide in Gas Phase by Sequential Injection Analysis Technique[J]. Anal Chim Acta, 2001,449(1):189-197.
11. [11]
  Bramanti E, D'Ulivo L, Lomonte C. Determination of Hydrogen Sulfide and Volatile Thiols in Air Samples by Mercury Probe Derivatization Coupled with Liquid Chromatography Atomic Fluorescence Spectrometry[J]. Anal Chim Acta, 2006,579(1):38-46. doi: 10.1016/j.aca.2006.07.004
12. [12]
  Ubuka T, Abe T, Kajikawa R. Determination of Hydrogen Sulfide and Acid-Labile Sulfur in Animal Tissues by Gas Chromatography and Ion Chromatography[J]. J Chromatogr B:Biomed Sci Appl, 2001,757(1):31-37. doi: 10.1016/S0378-4347(01)00046-9
13. [13]
  Tang L, Zheng Z, Zhong K. A 2, 5-Diaryl-1, 3, 4-Oxadiazole-Based Fluorescent Probe for Rapid and Highly Selective Recognition of Hydrogen Sulfide with a Large Stokes Shift Through Switching on ESIPT[J]. Tetrahedron Lett, 2016,57(12):1361-1364. doi: 10.1016/j.tetlet.2016.02.056
14. [14]
  Chen S, Hou P, Song X. A Red-Emitting Fluorescent Probe for Imaging Hydrogen Sulphide with a Large Stokes Shift[J]. Sens Actuators B:Chem, 2015,221:951-955. doi: 10.1016/j.snb.2015.07.020
15. [15]
  Zhang C, Peng B, Chen W. A Ratiometric Fluorescent Probe for Hydrogen Sulfide Based on the Nucleophilic Substitution-Cyclization of Diselenides[J]. Dyes Pigm, 2015,121:299-304. doi: 10.1016/j.dyepig.2015.06.003
16. [16]
  Chen Y, Zhu C, Yang Z. A Ratiometric Fluorescent Probe for Rapid Detection of Hydrogen Sulfide in Mitochondria[J]. Angew Chem Int Ed, 2013,125(6):1732-1735. doi: 10.1002/ange.v125.6
17. [17]
  Kumar N, Bhalla V, Kumar M. Recent Developments of Fluorescent Probes for the Detection of Gasotransmitters (NO, CO and H₂S)[J]. Coord Chem Rev, 2013,257(15):2335-2347.
18. [18]
  Huang Y, Zhang C, Xi Z. Synthesis and Characterizations of a Highly Sensitive and Selective Fluorescent Probe for Hydrogen Sulfide[J]. Tetrahedron, 2016,57(10):1187-1191. doi: 10.1016/j.tetlet.2016.02.017
19. [19]
  CHEN Hongrong, WU Ya'nan, CHEN Shiyan. "Naked-eye" and Fluorescence "Turn-on" Recognition of Al³⁺ Based on 2-Hydroxy-Naphthalene-Formaldehyde Benzoyl-Hydrazone Derivatives[J]. Chinees J Appl Chem, 2016,33(5):599-605. doi: 10.11944/j.issn.1000-0518.2016.05.150333
20. [20]
  Komatsu T, Urano Y, Fujikawa Y. Development of 2, 6-Carboxy-Substituted Boron Dipyrromethene (BODIPY) as a Novel Scaffold of Ratiometric Fluorescent Probes for Live Cell Imaging[J]. Chem Commun, 2009,45(45):7015-7017.
21. [21]
  Lim C S, Masanta G, Kim H J. Ratiometric Detection of Mitochondrial Thiols with a Two-Photon Fluorescent Probe[J]. J Am Chem Soc, 2011,133(29):11132-11135. doi: 10.1021/ja205081s
22. [22]
  Zhang J F, Lim C S, Bhuniya S. A Highly Selective Colorimetric and Ratiometric Two-Photon Fluorescent Probe for Fluoride Ion Detection[J]. Org Lett, 2011,13(5):1190-1193. doi: 10.1021/ol200072e
23. [23]
  Peng H, Cheng Y, Dai C. A Fluorescent Probe for Fast And Quantitative Detection of Hydrogen Sulfide in Blood[J]. Angew Chem Int Ed, 2011,50(41):9672-9675. doi: 10.1002/anie.201104236
24. [24]
  Sun W, Fan J, Hu C. A Two-Photon Fluorescent Probe with Near-Infrared Emission for Hydrogen Sulfide Imaging in Biosystems[J]. Chem Commun, 2013,49(37):3890-3892. doi: 10.1039/c3cc41244j
25. [25]
  Curiel D, Sánchez G, Más-Montoya M. Rational Design of a Fluorescent Receptor for the Recognition of Anthrax Biomarker Dipicolinate[J]. Analyst, 2012,137(23):5499-5501. doi: 10.1039/c2an35895f
26. [26]
  Liu Y, Fei Q, Shan H. 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(8):1868-1875. doi: 10.1039/c3an02230g
27. [27]
  Xu J, Zhang Y, Yu H. Mitochondria-Targeted Fluorescent Probe for Imaging Hydrogen Peroxide in Living Cells[J]. Anal Chem, 2015,88(2):1455-1461.
28. [28]
  Huang Z, Ding S, Yu D. Aldehyde Group Assisted Thiolysis of Dinitrophenyl Ether:A New Promising Approach for Efficient Hydrogen Sulfide Probes[J]. Chem Commun, 2014,50(65):9185-9187. doi: 10.1039/C4CC03818E
29. [29]
  Dale T J, Rebek J. Fluorescent Sensors for Organophosphorus Nerve Agent Mimics[J]. J Am Chem Soc, 2006,128(14):4500-4501. doi: 10.1021/ja057449i
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