Skip to main content
Log in

Ratiometric Probe for Rapid Naked Eye Detection of Toxic Hydrazine: Real Time Application in Strip Test, Spray Test and Soil Analysis

  • Original Article
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Striking colorimetric probe (CynH) for abrupt detection of hydrazine under complete aqueous solution was achieved. The water soluble probe was designed with electron “push–pull” strategy by coupling of 4-hydroxy benzaldehyde and 2, 3, 3-trimethylindolinine. The positively charged N-propylated indolinine make the probe completely soluble in water. The probe yields eye catching selective detection of hydrazine over other competing analytes with high sensitivity. Obvious colour change was observed from colourless to appearance of bright pink colour with hydrazine. It reacts quickly with hydrazine within 2 min and makes the probe an effective candidate for practical application. The real time application was demonstrated using paper strip to detect hydrazine vapour. This probe is superior to earlier reported probes because of its effective sensing of hydrazine displayed with various applications including real-time strip based sensing, spray test and soil analysis. In all the examinations, the probe yields distinct response with rapid naked eye colour change which overcomes the drawbacks of previous reports.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

Availability of Data and Material

Electronic supporting information file is available for synthesis procedure, NMR and MS analysis.

References

  1. Rosca V, Koper MT (2008) Electrocatalytic oxidation of hydrazine on platinum electrodes in alkaline solutions. Electrochim Acta 53:5199–5205. https://doi.org/10.1016/j.electacta.2008.02.054

    Article  CAS  Google Scholar 

  2. Yu L, Zhang X, Yu L (2014) On-line Determination of Hydrazine in Environmental Water by Reference Flow Injection Analysis. Communications in Information Science and Management Engineering., 4: 13, Book series, 1st edition, CRC press Taylor and francis, Editor: Garry Lee, Hong Kong

  3. Khaled K (2006) Experimental and theoretical study for corrosion inhibition of mild steel in hydrochloric acid solution by some new hydrazine carbodithioic acid derivatives. Appl Surf Sci 252:4120–4128. https://doi.org/10.1016/j.apsusc.2005.06.016

    Article  CAS  Google Scholar 

  4. Zelnick SD, Mattie DR, Stepaniak PC (2003) Occupational exposure to hydrazines: treatment of acute central nervous system toxicity. Aviat Space Environ Med 74:1285–1291

    PubMed  CAS  Google Scholar 

  5. Yin WX, Li ZP, Zhu JK, Qin HY (2008) Effects of NaOH addition on performance of the direct hydrazine fuel cell. J Power Sources 182:520–523. https://doi.org/10.1016/j.jpowsour.2008.04.028

    Article  CAS  Google Scholar 

  6. Aigner B, Darsow U, Grosber M, Ring J, Plötz S (2010) Multiple basal cell carcinomas after long-term exposure to hydrazine: Case report and review of the literature. Dermatology 221:300–302. https://doi.org/10.1159/000321338

    Article  PubMed  CAS  Google Scholar 

  7. Garrod S, Bollard ME, Nicholls AW, Connor SC, Connelly J, Nicholson JK, Holmes E (2005) Integrated metabonomic analysis of the multiorgan effects of hydrazine toxicity in the rat. Chem Res Toxicol 18:115–122. https://doi.org/10.1021/tx0498915

    Article  PubMed  CAS  Google Scholar 

  8. Umar A, Rahman MM, Kim SH, Hahn YB (2008) Zinc oxide nanonail based chemical sensor for hydrazine detection. Chem Comm 2:66–168. https://doi.org/10.1039/B711215G

    Article  Google Scholar 

  9. Cruz Vieira I, Omuro Lupetti K, Fatibello-Filho O (2002) Sweet potato (Ipomoea batatas (L.) Lam.) tissue as a biocatalyst in a paraffin/graphite biosensor for hydrazine determination in boiler feed water. Anal Lett 35:2221–2231. https://doi.org/10.1081/AL-120016097

    Article  CAS  Google Scholar 

  10. Reilly CA, Aust SD (1997) Peroxidase substrates stimulate the oxidation of hydralazine to metabolites which cause single-strand breaks in DNA. Chem Res Toxicol 10:328–334. https://doi.org/10.1021/tx960189l

    Article  PubMed  CAS  Google Scholar 

  11. Leakakos T, Shank RC (1994) Hydrazine genotoxicity in the neonatal rat. Toxicol Appl Pharm 126:295–300. https://doi.org/10.1006/taap.1994.1119

    Article  CAS  Google Scholar 

  12. Noda A, Ishizawa M, Ohno K, Sendo T, Noda H (1986) Relationship between oxidative metabolites of hydrazine and hydrazine-induced mutagenicity. Toxicol Lett 31:131–137. https://doi.org/10.1016/0378-4274(86)90006-8

    Article  PubMed  CAS  Google Scholar 

  13. Vivekanandan P, Gobianand K, Priya S, Vijayalakshmi P, Karthikeyan S (2007) Protective effect of picroliv against hydrazine-induced hyperlipidemia and hepatic steatosis in rats. Drug Chem Toxicol 30:241–252. https://doi.org/10.1080/01480540701375216

    Article  PubMed  CAS  Google Scholar 

  14. Oh JA, Park JH, Shin HS (2013) Sensitive determination of hydrazine in water by gas chromatography–mass spectrometry after derivatization with ortho-phthalaldehyde. Anal Chim Acta 769:79–83. https://doi.org/10.1016/j.aca.2013.01.036

    Article  PubMed  CAS  Google Scholar 

  15. Liu J, Li Y, Jiang J, Huang X (2010) C@ ZnO nanorod array-based hydrazine electrochemical sensor with improved sensitivity and stability. Dalton Trans 39:8693–8697. https://doi.org/10.1039/C0DT00258E

    Article  PubMed  CAS  Google Scholar 

  16. Li Y, Deng C, Yang M (2014) Facilely prepared composites of polyelectrolytes and graphene as the sensing materials for the detection of very low humidity. Sensors Actuat B: Chem 194:51–58. https://doi.org/10.1016/j.snb.2013.12.080

    Article  CAS  Google Scholar 

  17. Qian Y, Lin J, Han L, Lin L, Zhu H (2014) A resorufin-based colorimetric and fluorescent probe for live-cell monitoring of hydrazine. Biosens Bioelectron 58:282–286. https://doi.org/10.1016/j.bios.2014.02.059

    Article  PubMed  CAS  Google Scholar 

  18. Goswami S, Paul S, Manna A (2015) Fast and ratiometric naked eye detection of hydrazine for both solid and vapour phase sensing. New J Chem 39:2300–2305. https://doi.org/10.1039/C4NJ02220C

    Article  CAS  Google Scholar 

  19. Batchelor-McAuley C, Banks CE, Simm AO, Jones TG, Compton RG (2006) The electroanalytical detection of hydrazine: a comparison of the use of palladium nanoparticles supported on boron-doped diamond and palladium plated BDD microdisc array. Analyst 131:106–110. https://doi.org/10.1039/B513751A

    Article  PubMed  CAS  Google Scholar 

  20. Bhutani H, Singh S, Vir S, Bhutani K, Kumar R, Chakraborti AK, Jindal K (2007) LC and LC-MS study of stress decomposition behaviour of isoniazid and establishment of validated stability-indicating assay method. J Pharmaceut Biomed 43:1213–1220. https://doi.org/10.1016/j.jpba.2006.10.013

    Article  CAS  Google Scholar 

  21. Li K, Xu HR, Yu KK, Hou JT, Yu XQ (2013) A coumarin-based chromogenic and ratiometric probe for hydrazine. Anal Methods 5:2653–2656. https://doi.org/10.1039/C3AY40148K

    Article  CAS  Google Scholar 

  22. Zhang J, Ning L, Liu J, Wang J, Yu B, Liu X, Yao X, Zhang Z, Zhang H (2015) Naked-eye and near-infrared fluorescence probe for hydrazine and its applications in in vitro and in vivo bioimaging. Anal Chem 87:9101–9107. https://doi.org/10.1021/acs.analchem.5b02527

    Article  PubMed  CAS  Google Scholar 

  23. Sun M, Bai L, Liu DQ (2009) A generic approach for the determination of trace hydrazine in drug substances using in situ derivatization-headspace GC–MS. J Pharmaceut Biomed 49:529–533. https://doi.org/10.1016/j.jpba.2008.11.009

    Article  CAS  Google Scholar 

  24. Choi MG, Hwang J, Moon JO, Sung J, Chang SK (2011) Hydrazine-selective chromogenic and fluorogenic probe based on levulinated coumarin. Org Lett 13:5260–5263. https://doi.org/10.1021/ol202136q

    Article  PubMed  CAS  Google Scholar 

  25. Zhu S, Lin W, Yuan L (2013) Development of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells. Anal Methods 5:3450–3453. https://doi.org/10.1039/C3AY40540K

    Article  CAS  Google Scholar 

  26. Cui L, Peng Z, Ji C, Huang J, Huang D, Ma J, Zhang S, Qian X, Xu Y (2014) Hydrazine detection in the gas state and aqueous solution based on the Gabriel mechanism and its imaging in living cells. Chem Comm 50:1485–1487. https://doi.org/10.1039/C3CC48304E

    Article  PubMed  CAS  Google Scholar 

  27. Xiao L, Tu J, Sun S, Pei Z, Pei Y, Pang Y, Xu Y (2014) A fluorescent probe for hydrazine and its in vivo applications. RSC Adv 4:41807–41811. https://doi.org/10.1039/C4RA08101C

    Article  CAS  Google Scholar 

  28. Fan J, Sun W, Hu M, Cao J, Cheng G, Dong H, Song K, Liu Y, Sun S, Peng X (2012) An ICT-based ratiometric probe for hydrazine and its application in live cells. Chem Comm 48:8117–8119. https://doi.org/10.1039/C2CC34168A

    Article  PubMed  CAS  Google Scholar 

  29. Oyefusi A, Olanipekun O, Neelgund GM, Peterson D, Stone JM, Williams E, Carson L, Regisford G, Oki A (2014) Hydroxyapatite grafted carbon nanotubes and graphene nanosheets: Promising bone implant materials. Spectrochim Acta Part A Mol Biomol Spectrosc 132:410–416. https://doi.org/10.1016/j.saa.2014.04.004

    Article  CAS  Google Scholar 

  30. Sun M, Guo J, Yang Q, Xiao N, Li Y (2014) A new fluorescent and colorimetric sensor for hydrazine and its application in biological systems. J Mater Chem B 2:1846–1851. https://doi.org/10.1039/C3TB21753A

    Article  PubMed  CAS  Google Scholar 

  31. Tse H, Li Q, Chan S, You Q, Lee AW, Chan W (2016) A ratiometric fluorescent and colorimetric probe for selective detection of hydrazine. RSC Adv 6:14678–14681. https://doi.org/10.1039/C5RA26683A

    Article  CAS  Google Scholar 

  32. Ruan S, Gao Y, Wang Y, Li M, Yang H, Song J, Wang Z, Wang S (2020) A novel berberine-based colorimetric and fluorimetric probe for hydrazine detection. New J Chem 44:15752–15757. https://doi.org/10.1039/D0NJ03599H

    Article  CAS  Google Scholar 

  33. Fraga-Corral M, Carpena M, Garcia-Oliveira P, Pereira A, Prieto M, Simal-Gandara J (2020) Analytical metabolomics and applications in health, environmental and food science. Crit Rev Anal Chem 1–23. https://doi.org/10.1080/10408347.2020.1823811

  34. Mahapatra AK, Maji R, Maiti K, Manna SK, Mondal S, Ali SS, Manna S, Sahoo P, Mandal S, Uddin MR (2015) A BODIPY/pyrene-based chemodosimetric fluorescent chemosensor for selective sensing of hydrazine in the gas and aqueous solution state and its imaging in living cells. RSC Adv 5:58228–58236. https://doi.org/10.1039/C5RA10198K

    Article  CAS  Google Scholar 

  35. Ju Z, Li D, Zhang D, Li D, Wu C, Xu Z (2017) An ESIPT-based fluorescent probe for hydrazine detection in aqueous solution and its application in living cells. J Fluoresce 27:679–687. https://doi.org/10.1007/s10895-016-1997-7

    Article  CAS  Google Scholar 

  36. Hao Y, Zhang Y, Ruan K, Chen W, Zhou B, Tan X, Wang Y, Zhao L, Zhang G, Qu P (2017) A naphthalimide-based chemodosimetric probe for ratiometric detection of hydrazine. Sensors Actuat B: Chem 244:417–424. https://doi.org/10.1016/j.snb.2016.12.145

    Article  CAS  Google Scholar 

  37. Sun Y, Zhao D, Fan S, Duan L (2015) A 4-hydroxynaphthalimide-derived ratiometric fluorescent probe for hydrazine and its in vivo applications. Sensors Actuat B: Chem 208:512–517. https://doi.org/10.1016/j.snb.2014.11.057

    Article  CAS  Google Scholar 

  38. Liu C, Wang F, Xiao T, Chi B, Wu Y, Zhu D, Chen X (2018) The ESIPT fluorescent probes for N2H4 based on benzothiazol and their applications for gas sensing and bioimaging. Sensors Actuat B: Chem 256:55–62. https://doi.org/10.1016/j.snb.2017.09.198

    Article  CAS  Google Scholar 

  39. Ran YZ, Xu HR, Li K, Yu KK, Yang J, Yu XQ (2016) Development of a mitochondria-targeted fluorescent probe for hydrazine monitoring in living cells. RSC Adv 6:111016–111019. https://doi.org/10.1039/C6RA24110G

    Article  CAS  Google Scholar 

  40. Ma J, Fan J, Li H, Yao Q, Xia J, Wang J, Peng X (2017) Probing hydrazine with a near-infrared fluorescent chemodosimeter. Dyes Pigment 138:39–46. https://doi.org/10.1016/j.dyepig.2016.11.026

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Contributions

Sivan Velmathi contributed to the conception of the study and wrote the manuscript and Natarajan Vijay performed all the experiments and analysis and wrote the manuscript.

Corresponding author

Correspondence to Sivan Velmathi.

Ethics declarations

Consent to Participate

A statement regarding informed consent is not applicable.

Consent for Publication

A statement regarding informed consent is not applicable.

Conflicts of Interest

Not applicable.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 15.4 MB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vijay, N., Velmathi, S. Ratiometric Probe for Rapid Naked Eye Detection of Toxic Hydrazine: Real Time Application in Strip Test, Spray Test and Soil Analysis. J Fluoresc 31, 1917–1925 (2021). https://doi.org/10.1007/s10895-021-02825-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-021-02825-x

Keywords

Navigation