Journals / Black Sea Journal of Engineering and Science / 2025 / Cilt: 8 Sayı: 6

Synthesis and Characterization of Thiophene Cyclic Schiff Base Ligand and Metal Ion Complexes

Ali Çapan(Gaziantep Üniversitesi NMYO Gıda teknolojisi Programı)0000-0002-6477-6604
Mehmet Sönmez(GAZIANTEP UNIVERSITY, FACULTY OF ARTS AND SCIENCES)0000-0003-3127-666X
Pages
1864–1873
Publication Date
2025-11-15
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Moreover, the molar conductivities of the complexes were found to be in the range of 1.5–2.9 μS•cm⁻¹, indicating their non-electrolytic nature.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:In this study, a new Schiff base ligand (L) containing a thiophene ring was synthesized via the reaction of thiophene-2,5-dicarbaldehyde with 5-amino-1,3,4-thiadiazole-2-thiol.
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Key Findings & Data:The ligand (L) reacted with metal acetate salts [M(CH₃COO)₂; M = Cu, Co, Ni] in a 1:1 molar ratio to form metal complexes with the general formula [ML(CH₃COO)₂]•nH₂O (n = 2, 3).
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Conclusion & Impact:Moreover, the molar conductivities of the complexes were found to be in the range of 1.5–2.9 μS•cm⁻¹, indicating their non-electrolytic nature.
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:Thiophene · Thiadiazole · Schiff base

Abstract

In this study, a new Schiff base ligand (L) containing a thiophene ring was synthesized via the reaction of thiophene-2,5-dicarbaldehyde with 5-amino-1,3,4-thiadiazole-2-thiol. The structure of the ligand was elucidated using elemental analysis, FT-IR, NMR, and UV-Vis spectroscopy. The ligand (L) reacted with metal acetate salts [M(CH₃COO)₂; M = Cu, Co, Ni] in a 1:1 molar ratio to form metal complexes with the general formula [ML(CH₃COO)₂]•nH₂O (n = 2, 3). Structural characterization of the metal complexes was performed using elemental analysis, FT-IR, UV-Vis, TGA/DTA, electrolytic conductivity, and magnetic susceptibility measurements. Based on the obtained data, it was proposed that the Cu(II), Co(II), and Ni(II) complexes adopt a tetrahedral geometry. Moreover, the molar conductivities of the complexes were found to be in the range of 1.5–2.9 μS•cm⁻¹, indicating their non-electrolytic nature.

Özet

In this study, a new Schiff base ligand (L) containing a thiophene ring was synthesized via the reaction of thiophene-2,5-dicarbaldehyde with 5-amino-1,3,4-thiadiazole-2-thiol. The structure of the ligand was elucidated using elemental analysis, FT-IR, NMR, and UV-Vis spectroscopy. The ligand (L) reacted with metal acetate salts [M(CH₃COO)₂; M = Cu, Co, Ni] in a 1:1 molar ratio to form metal complexes with the general formula [ML(CH₃COO)₂]•nH₂O (n = 2, 3). Structural characterization of the metal complexes was performed using elemental analysis, FT-IR, UV-Vis, TGA/DTA, electrolytic conductivity, and magnetic susceptibility measurements. Based on the obtained data, it was proposed that the Cu(II), Co(II), and Ni(II) complexes adopt a tetrahedral geometry. Moreover, the molar conductivities of the complexes were found to be in the range of 1.5–2.9 μS•cm⁻¹, indicating their non-electrolytic nature.

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Cite This Article

Çapan, A., Hasan, A. E., Sönmez, M. (2025). Synthesis and Characterization of Thiophene Cyclic Schiff Base Ligand and Metal Ion Complexes. Black Sea Journal of Engineering and Science, Cilt: 8 Sayı: 6, 1864–1873. https://doi.org/10.34248/bsengineering.1725400

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References (30)

  1. Abdel Aziz AA, Seda SH. 2017. Synthesis, structural features and biochemical activity assessment of N,N′‐bis‐(2‐mercaptophenylimine)‐2,5‐thiophenedicarboxaldehyde Schiff base and its Co(II), Ni(II), Cu(II) and Zn(II) complexes. Appl Organomet Chem, 31(12): 3879. https://doi.org/10.1002/aoc.3879
  2. Abd-El-Aziz A, Li Z, Zhang X, Elnagdy S, Mansour MS, ElSherif A, Ma N, Abd-El-Aziz AS. 2025. Advances in coordination chemistry of Schiff base complexes: A journey from nanoarchitectonic design to biomedical applications. Top Curr Chem, 383(1): 1-102. https://doi.org/10.1007/s41061-025-00489-w
  3. Babu KA, Singhvi I, Ravindra N, Shaik AB. 2020. Antimicrobial and antitubercular evaluation of some new 5-amino-1,3,4-thiadiazole-2-thiol derived Schiff Bases. Rev Roum Chim, 65(9): 771-776. https://doi.org/10.33224/rrch.2020.65.9.01
  4. Bandi KR, Singh AK, Upadhyay A. 2014. Electroanalytical and naked eye determination of Cu²⁺ ion in various environmental samples using 5-amino-1,3,4-thiadiazole-2-thiol based Schiff bases. Mater Sci Eng C Mater Biol Appl, 34: 149-157. https://doi.org/10.1016/j.msec.2013.09.006
  5. Begum M, Puttaveerappa D, Marisamy VH, Dharmappa RN. 2022. Synthesis, characterization and larvicidal activity of Schiff base ligand 5-(((5-mercapto-1,3,4-thiadiazol-2-yl)imino)methyl)-2-methoxyphenol and its metal(II) complexes. SSRN. 4274113. https://doi.org/10.2139/ssrn.4274113
  6. Beytur M, Akyıldırım O, Aktaş Yokuş Ö. 2019. Synthesis, characterization and DFT calculations of 5-Mercapto-2-(3-methyl-thiophen-2-yl-methylidenamino)-1,3,4-thiadiazole compound. J Suleyman Demirel Univ Inst Sci, 23(2): 411-418. https://doi.org/10.19113/sdufenbed.500767
  7. Bingöl M, Turan N. 2020. Schiff base and metal(II) complexes containing thiophene-3-carboxylate: Synthesis, characterization and antioxidant activities. J Mol Struct, 1205: 127542. https://doi.org/10.1016/j.molstruc.2019.127542
  8. Capan A, Uruş S, Sönmez M. 2018. Ru (III), Cr (III), Fe (III) complexes of Schiff base ligands bearing phenoxy Groups: Application as catalysts in the synthesis of vitamin K3. J Saudi Chem Soc, 22(6): 757-766. https://doi.org/10.1016/j.jscs.2017.12.007
  9. Chandra S, Gautam S, Rajor HK, Bhatia R. 2015. Syntheses, spectroscopic characterization, thermal study, molecular modeling, and biological evaluation of novel Schiff’s base benzil bis(5-amino-1,3,4-thiadiazole-2-thiol) with Ni(II), and Cu(II) metal complexes. Spectrochim Acta A Mol Biomol Spectrosc, 137: 749-760. https://doi.org/10.1016/j.saa.2014.08.046
  10. Dhanapal P, Manju SL. 2024. Thiophene appended Schiff base probe for selective ‘turn-on’ response for copper(II) ion and their applications in live cell imaging. Synth Met, 309: 117752. https://doi.org/10.1016/j.synthmet.2024.117752
  11. Kumar M, Singh AK, Singh AK, Yadav RK, Singh S, Singh AP, Chauhan A. 2023. Recent advances in 3d-block metal complexes with bi, tri, and tetradentate Schiff base ligands derived from salicylaldehyde and its derivatives: Synthesis, characterization and applications. Coord Chem Rev, 488: 215176. https://doi.org/10.1016/j.ccr.2023.215176
  12. Miroslaw B. 2020. Homo- and hetero-oligonuclear complexes of platinum group metals (PGM) coordinated by imine Schiff base ligands. Int J Mol Sci, 21(10): 3493. https://doi.org/10.3390/ijms21103493
  13. Mishra G, Dwivedi PK, Verma N, Srivastava S, Singh AK, Chaturvedi D. 2023. p-TSA-promoted efficient synthesis of some new thiophene hybridized thiadiazolyl Schiff bases as antibacterial agents. Indian J Heterocycl Chem, 33(03): 361-368. https://doi.org/10.59467/IJHC.2023.33.361
  14. Pandey A, Rajavel R, Chandraker S, Dash D. 2012. Synthesis of Schiff bases of 2-amino-5-aryl-1,3,4-thiadiazole and its analgesic, anti-inflammatory and anti-bacterial activity. J Chem, 9(4): 2524-2531. https://doi.org/10.1155/2012/145028
  15. Pandey AK, Baboo V, Mishra VN, Singh VK, Dwivedi A. 2022. Comparative Study of Molecular Docking, Structural, Electronic, Vibrational Spectra and Fukui Function Studies of Thiadiazole Containing Schiff Base – A Complete Density Functional Study. Polycycl Aromat Compd 42: 13–39. https://doi.org/10.1080/10406638.2020.1712440
  16. Pervaiz M, Quratulain R, Ejaz A, Shain M, Saeed Z, Nasir S, Khan R, Ashraf AS, Younas U. 2023. Thiosemicarbazides, 1,3,4 thiadiazole Schiff base derivatives of transition metal complexes as antimicrobial agents. Inorg Chem Commun, 160: 111856. https://doi.org/10.1016/j.inoche.2023.111856
  17. Radha VP, Prabakaran M. 2022. Novel thiadiazole‐derived Schiff base ligand and its transition metal complexes: Thermal behaviour, theoretical study, chemo‐sensor, antimicrobial, antidiabetic and anticancer activity. App Org Chem, 36(11): 6872. https://doi.org/10.1002/aoc.6872
  18. Rajimon KJ, Alzahrani AY, Aazam ES, Abbas BM, Govindarajan P, Thomas R. 2024. Unveiling the multifaceted potential of (E)-N-(4-chlorophenyl)-1-(thiophen-2-yl)methanimine. J Mol Struct, 1302: 137428. https://doi.org/10.1016/j.molstruc.2023.137428
  19. Reeja J, Thomas KJ, Ragi K, Binsi MP. 2022. Screening of two sulphur-containing Schiff’s bases corrosion inhibition properties on CS: Gravimetric, electrochemical and quantum chemical studies. Port Electrochim Acta, 40: 223-241. https://doi.org/10.4152/pea.2022400401
  20. Rezki N, Al-Yahyawi A, Bardaweel S, Al-Blewi F, Aouad M. 2015. Synthesis of Novel 2,5-Disubstituted1,3,4-thiadiazoles Clubbed 1,2,4-Triazole, 1,3,4-Thiadiazole, 1,3,4-Oxadiazole and/or Schiff Base as Potential Antimicrobial and Antiproliferative Agents. Molecules, 20: 16048-16067. https://doi.org/10.3390/molecules200916048
  21. Saritha TJ, Metilda, P. 2021. Synthesis, spectroscopic characterization and biological applications of some novel Schiff base transition metal(II) complexes derived from curcumin moiety. J Saudi Chem Soc, 25(6): 101245. https://doi.org/10.1016/j.jscs.2021.101245
  22. Shaalan N, Khalaf WM, Mahdi S. 2022. Preparation and Characterization of New Tetra-Dentate; Schiff Base with Some of Metal Ions Complexes. Indones J Chem, 22 (1): 62-71. https://doi.org/10.22146/ijc.66118
  23. Shalinee, Kumar S. 2024. Eco-friendly synthesis, characterization, and antimicrobial evaluation of transition metal (II) complexes with Thiophene-Derived Tridentate (S N N Donor) Heterocyclic Schiff Base Ligand. Int Res J Pure Appl Chem, 25(6): 28-40. https://doi.org/10.9734/irjpac/2024/v25i6883
  24. Soliman AMM, Abd El Aleem Ali Ali El-Remaily M, Kamel MS, El-Araby A, Shokr EK. 2025. Synthesis and optical properties of Schiff base derivatives of thieno[2,3-b]thiophene-2,5-dicarbohydrazide. Sci Rep, 15(1): 1611. https://doi.org/10.1038/s41598-024-83994-0
  25. Soroceanu A, Bargan A. 2022. Advanced and biomedical applications of Schiff-base ligands and their metal complexes: A review. Crystals, 12(10): 1436. https://doi.org/10.3390/cryst12101436
  26. Suganya S, Velmathi S, Mubarak Ali D. 2014. Highly selective chemosensor for nanomolar detection of Cu²⁺ ion by fluorescent turn-on response and its application in living cells. Dyes Pigm, 104: 116-122. https://doi.org/10.1016/j.dyepig.2014.01.001
  27. Süleymanoğlu N, Demir EE, Direkel Ş, Ünver Y. 2020. Theoretical study and antimicrobial activities of New Schiff base derivatives with thiophene. J Mol Struct, 1218: 128522. https://doi.org/10.1016/j.molstruc.2020.128522
  28. Warad I, Bsharat O, Tabti S, Djedouani A, Al-Nuri M, Al-Zaqri N, Kumara K, Lokanath NK, Amereih S, Abu-Reidah IM. 2019. Crystal interactions, computational, spectral and thermal analysis of Schiff base ligand derived from thiophene. J Mol Struct, 1185: 290-299. https://doi.org/10.1016/j.molstruc.2019.02.109
  29. Xiong C, Li Y, Wang G, Fang L, Zhou S, Yao C, Chen Q, Zheng X, Qi D, Fu Y, Zhu Y. 2015. Selective removal of Hg(II) with polyacrylonitrile-2-amino-1,3,4-thiadiazole chelating resin. Chem Eng J, 259: 257-265. https://doi.org/10.1016/j.cej.2014.07.114
  30. Zhang R, Wang Q, Li Q, Ma C. 2009. Syntheses and characterization of triorganotin(IV) complexes of Schiff base derived from 4-amino-5-phenyl-1,2,4-triazole and 5-amino-1,3,4-thiadiazole. Inorg Chim Acta, 362: 2762-2769. https://doi.org/10.1016/j.ica.2008.12.017