Skip to main content
SpringerLink
Log in

An Isoniazid Based Schiff Base Sensor for Selective Detection of Pd2+ Ions

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

Abstract

Here, we developed a novel isoniazid based fluorescent probe (E)-N’-(thiophen-2-ylmethylene)isonicotinohydrazide (TINH) through simple condensation reaction and employed for selective detection of Pd2+ ions with a low detection limit of 4.102 × 10–11 M. Among the many existing cations, TINH bound Pd2+ ions with an association affinity of 9.794 × 105 M−1. Adding Pd2+ ions to ligand solution increased the absorption intensity in UV–Visible and quenched the emission intensity in fluorescence spectroscopic experiments. More importantly, this TINH complexed to Pd2+ ions in 1:1 stoichiometric ratio. To evaluate the stability of complexed system, pH experiments has been performed. The binding insights among the ligand and Pd2+ ions has been confirmed by IR spectroscopic and MASS spectrometric methods. Additionally, TINH also applied to real water samples for the identification and measurement of Pd2+ ions. Hence, this system could be highly applicable for detection of Pd2+ ions in environmental and industrial samples with in low detection range.

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

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
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

Availability of Data and Materials

Data and materials are available on demand.

References

  1. Maharramov AM, Mahmudov KT, Kopylovich MN, Pombeiro AJ (2016) Non-covalent interactions in the synthesis and design of new compounds. John Wiley & Sons

  2. Kumar A, Saini M, Mohan B, Kamboj M (2022) Colorimetric and fluorescent Schiff base sensors for trace detection of pollutants and biologically significant cations: A review (2010–2021). Microchem J 107798

  3. Qiu J, Jiang S, Lin B, Guo H, Yang F (2019) An unusual AIE fluorescent sensor for sequentially detecting Co2+-Hg2+-Cu2+ based on diphenylacrylonitrile Schiff-base derivative. Dyes Pigm 170:107590

    Article  CAS  Google Scholar 

  4. Bregović VB, Basarić N (2015) Anion binding with urea and thiourea derivatives. Coord Chem Rev 295:80–124

    Article  Google Scholar 

  5. Frost MC, Meyerhoff ME (2015) Real-time monitoring of critical care analytes in the bloodstream with chemical sensors: progress and challenges. Annu Rev Anal Chem 8:171–192

    Article  CAS  Google Scholar 

  6. Volesky B (1990) Removal and recovery of heavy metals. Biosorption Heavy Met 7–43

  7. Melentiev R, Yudhanto A, Tao R, Vuchkov T, Lubineau G (2022) Metallization of polymers and composites: State-of-the-art approaches. Mater Des 110958

  8. Pawlak J, Łodyga-Chruścińska E, Chrustowicz J (2014) Fate of platinum metals in the environment. J Trace Elem Med Biol 28:247–254

    Article  CAS  PubMed  Google Scholar 

  9. Kielhorn J, Melber C, Keller D, Mangelsdorf I (2002) Palladium–a review of exposure and effects to human health. Int J Hyg Environ Health 205:417–432

    Article  CAS  PubMed  Google Scholar 

  10. Reşitoğlu İA, Altinişik K, Keskin A (2015) The pollutant emissions from diesel-engine vehicles and exhaust after-treatment systems. Clean Technol Environ Policy 17:15–27

    Article  Google Scholar 

  11. Beletskaya IP, Alonso F, Tyurin V (2019) The Suzuki-Miyaura reaction after the Nobel prize. Coord Chem Rev 385:137–173

    Article  CAS  Google Scholar 

  12. Fleckenstein CA, Plenio H (2007) 9-Fluorenylphosphines for the Pd-catalyzed sonogashira, suzuki, and buchwald–hartwig coupling reactions in organic solvents and water. Chem Eur J 13:2701–2716

    Article  CAS  PubMed  Google Scholar 

  13. Mahata S, Bhattacharya A, Kumar JP, Mandal BB, Manivannan V (2020) Naked-eye detection of Pd2+ ion using a highly selective fluorescent heterocyclic probe by “turn-off” response and in-vitro live cell imaging. J Photochem Photobiol, A 394:112441

    Article  CAS  Google Scholar 

  14. Kumar A, Mohan B, Solovev AA, Saini M, Sharma HK (2022) Development of 2-hydroxy-naphthaldehyde functionalized Schiff base chemosensor for spectroscopic and colorimetric detection of Cu2+ and Pd2+ ions. Microchem J 180:107561

    Article  CAS  Google Scholar 

  15. Song F, Garner AL, Koide K (2007) A highly sensitive fluorescent sensor for palladium based on the allylic oxidative insertion mechanism. J Am Chem Soc 129:12354–12355

    Article  CAS  PubMed  Google Scholar 

  16. Liang G, Cai Q, Zhu W, Xu Y, Qian X (2015) A highly selective heterogeneous fluorescent sensor for palladium ions. Anal Methods 7:4877–4880

    Article  CAS  Google Scholar 

  17. Alqarni SA (2022) A review on conducting polymers for colorimetric and fluorescent detection of noble metal ions (Ag+, Pd2+, Pt2+/4+, and Au3+). Crit Rev Anal Chem 1–12

  18. Wang R, Yu Z (2007) Validity and reliability of Benesi-Hildebrand method. Acta Phys Chim Sin 23:1353–1359

    Article  CAS  Google Scholar 

  19. Zorn ME, Gibbons RD, Sonzogni WC (1999) Evaluation of approximate methods for calculating the limit of detection and limit of quantification. Environ Sci Technol 33:2291–2295

    Article  CAS  Google Scholar 

  20. Prakash O, Hussain K, Aneja DK, Sharma C, Aneja KR (2011) A facile iodine (III)-mediated synthesis of 3-(3-aryl-1-phenyl-1 H-pyrazol-4-yl)-[1, 2, 4] triazolo [4, 3-a] pyridines via oxidation of 2-((3-aryl-1-phenyl-1 H-pyrazol-4-yl) methylene)-1-(pyridin-2-yl) hydrazines and their antimicrobial evaluations. Org Med Chem Lett 1:1–9

    Article  PubMed  PubMed Central  Google Scholar 

  21. Chen S-Y, Li Z, Li K, Yu X-Q (2021) Small molecular fluorescent probes for the detection of lead, cadmium and mercury ions. Coord Chem Rev 429:213691

    Article  CAS  Google Scholar 

  22. Yu C, Chen L, Zhang J, Li J, Liu P, Wang W, Yan B (2011) “Off-On” based fluorescent chemosensor for Cu2+ in aqueous media and living cells. Talanta 85(3):1627–1633

    Article  CAS  PubMed  Google Scholar 

  23. Aggarwal R, Kumar S, Kumar A, Mohan B, Sharma D, Kumar V (2022) Development of heterocyclic 2, 7-diamino-3-phenylazo-6-phenylpyrazolo [1, 5-a] pyrimidine as antimicrobial agent and selective probe for UV–visible and colorimetric detection of Hg2+ ions. Microchem J 183:107991

    Article  CAS  Google Scholar 

  24. Renny JS, Tomasevich LL, Tallmadge EH, Collum DB (2013) Method of continuous variations: applications of job plots to the study of molecular associations in organometallic chemistry. Angew Chem Int Ed 52:11998–12013

    Article  CAS  Google Scholar 

  25. Adak AK, Purkait R, Manna SK, Ghosh BC, Pathak S, Sinha C (2019) Fluorescence sensing and intracellular imaging of Pd2+ ions by a novel coumarinyl-rhodamine Schiff base. New J Chem 43:3899–3906

    Article  CAS  Google Scholar 

  26. Mahapatra AK, Manna SK, Maiti K, Mondal S, Maji R, Mandal D, Mandal S, Uddin MR, Goswami S, Quah CK (2015) An azodye–rhodamine-based fluorescent and colorimetric probe specific for the detection of Pd2+ in aqueous ethanolic solution: synthesis, XRD characterization, computational studies and imaging in live cells. Analyst 140:1229–1236

    Article  CAS  PubMed  Google Scholar 

  27. Bhanja AK, Mishra S, Saha KD, Sinha C (2017) A fluorescence ‘turn-on’chemodosimeter for the specific detection of Pd2+ by a rhodamine appended Schiff base and its application in live cell imaging. Dalton Trans 46:9245–9252

    Article  CAS  PubMed  Google Scholar 

  28. Liu F, Du J, Xu M, Sun G (2016) A highly sensitive fluorescent sensor for palladium and direct imaging of its ecotoxicity in living model organisms. Chem Asian J 11:43–48

    Article  CAS  PubMed  Google Scholar 

  29. Huang Q, Zhou Y, Zhang Q, Wang E, Min Y, Qiao H, Zhang J, Ma T (2015) A new “off–on” fluorescent probe for Pd2+ in aqueous solution and live-cell based on spirolactam ring-opening reaction. Sens Actuators, B Chem 208:22–29

    Article  CAS  Google Scholar 

  30. Chen Y, Chen B, Han Y (2016) A novel rhodamine-based fluorescent probe for the fluorogenic and chromogenic detection of Pd2+ ions and its application in live-cell imaging. Sens Actuators B Chem 237:1–7

    Article  CAS  Google Scholar 

  31. Yang M, Bai Y, Meng W, Cheng Z, Su N, Yang B (2014) A novel selective fluorescent and colorimetric chemosensor for the visual detection of Pd2+ and application of imaging in living cells. Inorg Chem Commun 46:310–314

    Article  CAS  Google Scholar 

  32. Li H, Fan J, Song F, Zhu H, Du J, Sun S, Peng X (2010) Fluorescent probes for Pd2+ detection by allylidene–hydrazone ligands with excellent selectivity and large fluorescence enhancement. Chem Eur J 16:12349–12356

    Article  CAS  PubMed  Google Scholar 

  33. Wu H, Lin L, Zheng L, Guo H, Yang F (2022) Dual-response fluorescence sensor for detecting Cu2+ and Pd2+ based on bis-tetraphenylimidazole Schiff-base. J Photochem Photobiol A 432:114076

    Article  CAS  Google Scholar 

  34. Kang M, Jiang S, Liu Y, Wei K, Liu P, Yang X, Pei M, Zhang G (2023) A new “off-on-off” Schiff base from quinoline and thiophene as a fluorescent sensor for sequential monitoring Ga3+ and Pd2+. J Photochem Photobiol A 438:114510

    Article  CAS  Google Scholar 

  35. Zhou W, Gao Q, Liu D, Li C, Liu S, Xia K, Han B, Zhou C (2020) A single molecular sensor for selective and differential colorimetric/ratiometric detection of Cu2+ and Pd2+ in 100% aqueous solution. Spectrochim Acta Part A Mol Biomol Spectrosc 237:118365

    Article  CAS  Google Scholar 

  36. Chen H, Jin X, Lu H, Shen W (2018) A new rhodamine B-based ‘off-on’colorimetric chemosensor for Pd2+ and its imaging in living cells. Inorg Chim Acta 482:122–129

    Article  CAS  Google Scholar 

  37. Mohan B, Kumar S, Modi K, Deshmukh AH, Kumar A (2021) 2-((E)-1-((E)-(2-methoxybenzylidene) hydrazono) ethyl) phenol based cost-effective sensor for the selective detection of Eu3+ ions. Polyhedron 209:115460

    Article  Google Scholar 

  38. Chakraborty P, Rana A, Mukherjee S, Biswas S (2022) Metal–organic-framework-based chemosensor for ultrafast and ultrasensitive detection of Pd2+ ions in water, real specimens, and test strips. Inorg Chem 62(2):802–809

    Article  PubMed  Google Scholar 

Download references

Acknowledgements

The authors are thankful to the Department of chemistry, Baba Mastnath University, Asthal Bohar, Rohtak and the Department of chemistry, Kurukshetra University, Kurukshetra (India), for providing spectral facilities, including NMR spectroscopy.

Funding

There is no funding for this work.

Author information

Author notes

  1. Jasbir Singh and Shubham Saini are equally contributed to the manuscript.

Authors and Affiliations

  1. Department of Chemistry, Baba Mastnath University, Rohtak, 124021, India

    Jasbir Singh & Pallavi Bhardwaj

  2. Bharat Institute of Pharmacy Degree Course, Pehladpur, Babain-Kurukshetra, 136132, India

    Shubham Saini

  3. Department of Chemistry, Indira Gandhi National College, Ladwa, Kurukshetra, 136132, India

    Ravish K. Chauhan

  4. Department of Chemistry, Kurukshetra University Kurukshetra, Kurukshetra, 136119, India

    Ashwani Kumar

  5. Department of Chemistry, Deenbandhu Chhotu Ram University of Science & Technology, Murthal, Sonepat, 131039, Haryana, India

    Virender .

Authors
  1. Jasbir Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shubham Saini
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ravish K. Chauhan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pallavi Bhardwaj
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ashwani Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Virender .
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Jasbir Singh: Conceptualization, Investigation, Experimental, Resources, Formal analysis; Shubham Saini: Experimental, Formal analysis & Editing; Ravish K. Chauhan: Resources, Formal analysis; Writing- Original draft preparation; Pallavi Bhardwaj: Conceptualization, Investigation, Resources, Formal analysis; Ashwani Kumar: Writing- Original draft preparation, Formal analysis; Virender: Experimental, Writing- Original draft preparation, Formal analysis.

Corresponding authors

Correspondence to Ravish K. Chauhan or Pallavi Bhardwaj.

Ethics declarations

Ethical Approval

No such data applies to human and/ or animal studies. This work is a novel and has not been published in any journal or thesis 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.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 621 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

Singh, J., Saini, S., Chauhan, R.K. et al. An Isoniazid Based Schiff Base Sensor for Selective Detection of Pd2+ Ions. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03491-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10895-023-03491-x

Keywords

Search

Navigation