SpringerLink
Log in

Fluorescence Recognition of Hydrazine Driven by Neighboring Group Participation

  • RESEARCH
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Hydrazine (N2H4) has toxic effects on the environment. Although a variety of reactive probes have been used to identify hydrazine, practical applications required continuous development of hydrazine fluorescent probes with improved performance. Here, we applied the neighboring group participation (NGP) to the design of a fluorescent probe for hydrazine. The probe exhibited a rapid response to N2H4 and strong anti-interference ability, with detection limited to 0.031 μmol/L. Theoretical calculation showed that the energy barrier could be reduced by NGP. The cyclic intermediate formed by the indole ring and the α-ester carbonyl group significantly reduced the activation energy of the reaction. Practically, the probe could detect hydrazine in actual water samples.

Graphical Abstract

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 2
Fig. 5

Data Availability

Data is provided within the manuscript or supplementary information files.

References

  1. Ragnarsson U (2001) Synthetic methodology for alkyl substituted hydrazines. Chem Soc Rev 30(4):205–213. https://doi.org/10.1039/b010091a

    Article  Google Scholar 

  2. Gu HX, Ran R, Zhou W, Shao ZP, ** WQ, Xu NP, Ahn J (2008) Solid-oxide fuel cell operated on in situ catalytic decomposition products of liquid hydrazine. J Power Sources 177:323–329. https://doi.org/10.1016/j.jpowsour.2007.11.062

    Article  Google Scholar 

  3. Belghiti ME, Echihi S, Dafali A, Karzazi Y, Bakasse M, Elalaoui-Elabdallaoui H, Olasunkanmi LO, Ebenso EE, Tabyaoui M (2019) Computational simulation and statistical analysis on the relationship between corrosion inhibition efficiency and molecular structure of some hydrazine derivatives in phosphoric acid on mild steel surface. Appl Surf Sci 491:707–722. https://doi.org/10.1016/j.apsusc.2019.04.125

    Article  Google Scholar 

  4. 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  Google Scholar 

  5. Steinhoff D, Mohr U (1988) The question of carcinogenic effects of hydrazine. Exp Pathol 33:133–143. https://doi.org/10.1016/s0232-1513(88)80060-4

    Article  PubMed  Google Scholar 

  6. U.S. Environmental Protection Agency (EPA), Integrated Risk Information System (IRIS) on Hydrazine/Hydrazine Sulfate, National Center for Environmental Assessment, Office of Research and Development, Washington, DC, 1999

  7. Guo LL, Yang L, Li MY, Kuang LJ, Song YH, Wang L (2021) Covalent organic frameworks for fluorescent sensing: Recent developments and future challenges. Coord Chem Rev 440:213957. https://doi.org/10.1016/j.ccr.2021.213957

    Article  Google Scholar 

  8. Wang R, Bian ZC, Zhan DX, Wu ZY, Yao QQ, Zhang GM (2021) Boronic acid-based sensors for small-molecule reactive species: A review. Dyes Pigm 185:108885. https://doi.org/10.1016/j.dyepig.2020.108885

    Article  Google Scholar 

  9. Wang Y, Xue XL, Zhang Q, Wang KP, Chen SJ, Tang LS, Hu ZQ (2022) A hemicyanine-based near-infrared fluorescent probe for vapor-phase hydrazine detection and bioimaging in a complete aqueous media. Spectrochim Acta Part A 279:121406. https://doi.org/10.1016/j.saa.2022.121406

    Article  Google Scholar 

  10. Fu DQ, Wang XD, Liu B (2024) Old drug, new use: The thalidomide-based fluorescent probe for hydrazine detection. Spectrochim Acta Part A 309:123808. https://doi.org/10.1016/j.saa.2023.123808

    Article  Google Scholar 

  11. **ng MM, Han YY, Zhu YL, Sun YT, Shan YY, Wang KN, Liu QX, Dong BL, Cao DX, Lin WY (2022) Two ratiometric fluorescent probes based on the hydroxyl coumarin chalcone unit with large fluorescent peak shift for the detection of hydrazine in living cells. Anal Chem 94:12836–12844. https://doi.org/10.1021/acs.analchem.2c02798

    Article  PubMed  Google Scholar 

  12. Wu XM, Li YN, Yang SX, Tian HY, Sun BG (2020) A multiple-detection-point fluorescent probe for the rapid detection of mercury (II), hydrazine and hydrogen sulphide. Dyes Pigm 174:108056. https://doi.org/10.1016/j.dyepig.2019.108056

    Article  Google Scholar 

  13. Fan FG, Xu CY, Liu XN, Zhu MQ, Wang Y (2022) A novel ESIPT-based fluorescent probe with dual recognition sites for the detection of hydrazine in the environmental water samples and in-vivo bioimaging. Spectrochim Acta Part A 280:121499. https://doi.org/10.1016/j.saa.2022.121499

    Article  Google Scholar 

  14. Zhu MQ, Zhao ZY, Huang Y, Fan FG, Wang F, Li WL, Wu XW, Hua RM, Wang Y (2021) Hydrazine exposure: A near-infrared ICT-based fluorescent probe and its application in bioimaging and sewage analysis. Sci Total Environ 759:143102. https://doi.org/10.1016/j.scitotenv.2020.143102

    Article  PubMed  Google Scholar 

  15. Suna G, Gunduz S, Topal S, Ozturk T, Karakus E (2023) A unique triple–channel fluorescent probe for discriminative detection of cyanide, hydrazine, and hypochlorite. Talanta 257:124365. https://doi.org/10.1016/j.talanta.2023.124365

    Article  PubMed  Google Scholar 

  16. Guo ZR, Niu QF, Yang QX, Li TD, Wei T, Yang L, Chen JB, Qin XY (2020) New “naked-eye” colori/fluorimetric “turn-on” chemosensor: Ultrafast and ultrasensitive detection of hydrazine in ~100% aqueous solution and its bio-imaging in living cells. Anal Chim Acta 1123:64–72. https://doi.org/10.1016/j.aca.2020.04.079

    Article  PubMed  Google Scholar 

  17. Shan XF, Wu ST, Shen LY, Peng SL, Xu H, Wang ZY, Yang XJ, Huang YL, Feng X, Redshaw C, Zhang QL (2023) Ratiometric red aggregation-induced emission luminogens for hydrazine hydrate detection. Dyes Pigm 219:111609. https://doi.org/10.1016/j.dyepig.2023.111609

    Article  Google Scholar 

  18. Mu S, Gao H, Li C, Li SS, Wang YY, Zhang Y, Ma CM, Zhang HX, Liu XY (2021) A dual-response fluorescent probe for detection and bioimaging of hydrazine and cyanide with different fluorescence signals. Talanta 221:121606. https://doi.org/10.1016/j.talanta.2020.121606

    Article  PubMed  Google Scholar 

  19. Zhang YK, Xu C, Sun H, Ai JD, Ren MG (2023) A turn-on fluorescent probe for sensing N2H4 in living cells, zebrafishes and plant root with a large turn-on fluorescence signal. Talanta 265:124902. https://doi.org/10.1016/j.talanta.2023.124902

    Article  PubMed  Google Scholar 

  20. Guo ZB, Wang M, Li XY, Jia X, Wang XL, Zhang PZ, Wei C, Li XL (2020) A hepatocyte-targeting fluorescent probe for imaging isoniazidinduced hydrazine in HepG2 cells and zebrafish. Chem Commun 56: 14183–14186. http://pubs.rsc.org/en/ content/articlepdf/2020/CC/D0CC05330A

  21. Tang LJ, Zhou L, Liu AJ, Yan XM, Zhong KL, Liu XY, Gao X, Li JR (2021) A new cascade reaction-based colorimetric and fluorescence “turn on” dual-function probe for cyanide and hydrazine detection. Dyes Pigm 186:109034. https://doi.org/10.1016/j.dyepig.2020.109034

    Article  Google Scholar 

  22. Tiensomjitr K, Noorat R, Chomngam S, Wechakorn K, Prabpai S, Kanjanasirirat P, Pewkliang Y, Borwornpinyo S, Kongsaeree P (2018) A chromogenic and fluorogenic rhodol-based chemosensor for hydrazine detection and its application in live cell bioimaging. Spectrochim. Acta Part A 195: 136–141. https://www.sciencedirect.com/science/article/pii/S1386142518300507

  23. Rajalakshmi K, Muthusamy S, Lee HJ, Kannan P, Zhu DW, Song JW, Nam YS, Heo DN, Kwonf IK, Luo ZB, Xu YG (2024) Dual-channel fluorescent probe for discriminative detection of H2S and N2H4: Exploring sensing mechanism and real-time applications. J Hazard Mater 465:133036. https://doi.org/10.1016/j.jhazmat.2023.133036

    Article  PubMed  Google Scholar 

  24. Rajalakshmi K, Muthusamy S, Lee HJ, Kannan P, Zhu DW, Lodi RS, **e M, **e JM, Song JW, Xu YG (2024) Quinoline-derived electron-donating/withdrawing fluorophores for hydrazine detection and applications in environment and bioimaging. Spectrochim Acta Part A 304:123282. https://doi.org/10.1016/j.saa.2023.123282

    Article  Google Scholar 

  25. Muthusamy S, Yin SQ, Rajalakshmi K, Meng SC, Zhu DW, **e M, **e JM, Lodi RS, Xu YG (2022) Development of a quinoline-derived turn-on fluorescent probe for real time detection of hydrazine and its applications in environment and bioimaging. Dyes Pigm 206:110618. https://doi.org/10.1016/j.dyepig.2022.110618

    Article  Google Scholar 

  26. Zhu DW, Rajalakshmi K, Wang RQ, Wu HJ, Kannan P, Song JW, Lee HJ, Muthusamy S (2023) A coumarin derivative-based turn-on fluorescent probe for real-time applications of hydrazine detection in environment and bioimaging. Dyes Pigm 216:111370. https://doi.org/10.1016/j.dyepig.2023.111370

    Article  Google Scholar 

  27. Erdemir S, Malkondu S, Oguz M, Kocyigit O (2024) A novel pathway for ratiometric hydrazine sensing in environmental samples and the detection of intracellular viscosity by a mitochondria-targeted fluorescent sensor. Talanta 267:125143. https://doi.org/10.1016/j.talanta.2023.125143

    Article  PubMed  Google Scholar 

  28. ** Y, Sun RT, Li GQ, Yuan M, Shao WC, Cao MH, Yuan C, Wang SH (2023) Water-soluble single molecular probe for simultaneous detection of viscosity and hydrazine. Spectrochim Acta Part A 294:122558. https://doi.org/10.1016/j.saa.2023.122558

    Article  Google Scholar 

  29. Ramdular A, Woerpel KA (2020) Using neighboring-group participation for acyclic stereocontrol in diastereoselective substitution reactions of acetals. Org Lett 22:4113–4117. https://doi.org/10.1021/acs.orglett.0c01166

    Article  PubMed  PubMed Central  Google Scholar 

  30. Beaver MG, Billings SB, Woerpel KA (2008) C-glycosylation reactions of sulfur-substituted glycosyl donors: evidence against the role of neighboring-group participation. J Am Chem Soc 130:2082–2086. https://doi.org/10.1021/ja0767783

    Article  PubMed  Google Scholar 

Download references

Acknowledgements

We are grateful for the financial support from the Hebei University Talent Introduction Project, Hebei University Scientific Research Innovation Team (Science and Technology) (No. IT 2023B01).

Funding

The study was supported by the Hebei University Talent Introduction Project, Hebei University Scientific Research Innovation Team (Science and Technology) (No. IT 2023B01).

Author information

Authors and Affiliations

  1. Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry & Materials Science, Hebei University, Baoding, 071002, PR China

    Wenzhi Xu, Xue Li, Shuo Wang, Honglei Zhang & Wei Li

Authors
  1. Wenzhi Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xue Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shuo Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Honglei Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Wenzhi Xu wrote the main manuscript text. Xue Li synthesized the probe. Shuo Wang made a spectral titration. Honglei Zhang studied the practical application of the probe. Wei Li provided the funds.

Corresponding authors

Correspondence to Wenzhi Xu or Wei Li.

Ethics declarations

Ethics Approval

There is no ethic approval required for this research work.

Competing Interests

The authors declare no competing interests.

Additional information

Publisher's Note

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

Highlights

Ortho group was involved in hydrazine recognition.

The LOD was 0.031 μM.

The adjacent group effect was verified by calculation.

The probe could quantitatively detect hydrazine in tap water.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOC 2182 KB)

Supplementary file2 (DOC 841 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xu, W., Li, X., Wang, S. et al. Fluorescence Recognition of Hydrazine Driven by Neighboring Group Participation. J Fluoresc (2024). https://doi.org/10.1007/s10895-024-03782-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10895-024-03782-x

Keywords

Search

Navigation