Skip to main content
Log in

Synthesis of pyrimidine Schiff base transition metal complexes: characterization, spectral and electrochemical analyses, and photoluminescence properties

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

This study includes the synthesis, characterization, electrochemical analysis and photoluminescence properties of a Schiff base ligand bearing a pyrimidine ring and its Co(II), Ni(II), Cu(II) and Pd(II) metal complexes. The Schiff base ligand was derived from the condensation reaction of a pyrimidine amine with 2-hydroxy-1-naphthaldehyde. The structures were characterized using FT-IR, UV–Vis, elemental analysis, magnetic susceptibility and electrolytic conductivity. The ligand and its metal complexes displayed strong violet emissions upon UV exposure. The photoluminescence quantum yield and excited-state decay were measured for the ligand and its complexes. The excited-state lifetime for the ligand was 3.70 ns and its quantum yield of luminescence was found to be 0.40. A reduction in photoluminescence intensity and quantum yield was observed upon metal ion complexation. The compounds synthesized were studied by cyclic voltammetry to probe the existence of electrochemical reduction and oxidation processes.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. R. Hernández-Molina, A. Mederos, in Comprehensive Coordination Chemistry II, vol. 1, ed. by J.A. McCleverty, T.J. Meyer (Elsevier, Amsterdam, 2004), p. 411

    Google Scholar 

  2. M. Andruh, F. Tuna, in Focus on Organometallic Chemistry Research, ed. by M.A. Cato (Nova Publishers, Hauppauge, 2005), p. 144

    Google Scholar 

  3. A.J. Atkins, D. Black, A.J. Blake, A. Marin-Bocerra, S. Parsons, L. Ruiz-Ramirez, M. Schröder, Chem. Commun. 4, 457 (1996)

    Article  Google Scholar 

  4. P.A. Vigato, S. Tamburini, Coord. Chem. Rev. 248, 1717 (2004)

    Article  CAS  Google Scholar 

  5. P.A. Vigato, S. Tamburini, L. Bertolo, Coord. Chem. Rev. 251, 1311 (2007)

    Article  CAS  Google Scholar 

  6. M. Sakamoto, K. Maneski, H. Okawa, Coord. Chem. Rev. 219–221, 379 (2001)

    Article  Google Scholar 

  7. G. Ceyhan, C. Celik, S. Urus, I. Demirtas, M. Elmastas, M. Tümer, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 81(1), 184 (2011)

    Article  CAS  Google Scholar 

  8. R. Herchel, I. Nemec, M. Machata, Z. Trávníček, Inorg. Chem. 54(17), 8625 (2015)

    Article  CAS  PubMed  Google Scholar 

  9. N.S. Youssef, E.A. El-Zahany, M.A. El-Seidy, J. Phosphorus Sulfur Silicon Relat. Elem. 185(4), 785 (2010)

    Article  CAS  Google Scholar 

  10. N.K. Chaudhary, P. Mishra, Bioinorg. Chem. Appl. 2017, 1 (2017)

    Article  CAS  Google Scholar 

  11. R. Herchel, I. Nemec, M. Machata, Z. Trávníček, J. Sep. Sci. Technol. 52(6), 1052 (2017)

    Article  CAS  Google Scholar 

  12. A.D. Garnovskii, A.L. Nivorozhkin, V.I. Minkin, Coord. Chem. Rev. 126, 1 (1993)

    Article  CAS  Google Scholar 

  13. M. Valcarcel, M.D. Laque de Castro, Flow-Throgh Biochemical Sensors (Elsevier, Amsterdam, 1994)

    Google Scholar 

  14. U. Spichiger-Kelle, Chemical Sensors and Biosensors for Medical and Biological Applications (Wiley, Weinheim, 1998)

    Book  Google Scholar 

  15. J.F. Lawrence, R.W. Frei, Chemical Derivatization in Chromatography (Elsevier, Amsterdam, 1976)

    Google Scholar 

  16. M. Sönmez, M. Çelebi, I. Berber, Eur. J. Med. Chem. 45, 1935 (2010)

    Article  CAS  PubMed  Google Scholar 

  17. J.I. Pyo, E.J. Hwang, C.S. Cheong, S.H. Lee, S.W. Lee, I.T. Kim, S.H. Lee, Synth. Met. 155, 461 (2005)

    Article  CAS  Google Scholar 

  18. H. Lee, J. Oh, H.Y. Chu, J.-I. Lee, S.H. Kim, Y.S. Yang, G.H. Kim, L.M. Do, T. Zyung, J. Lee, Y. Park, Tetrahedron 59, 2773 (2003)

    Article  CAS  Google Scholar 

  19. K.W. Xue, B.Y. Chen, G.G. Han, Y. Duan, P. Chen, Y.Q. Yang, Y.H. Duan, X. Wang, Y. Zhao, Org. Electron. 22, 122 (2015)

    Article  CAS  Google Scholar 

  20. J.Y. Song, S.N. Park, S.J. Lee, Y.K. Kim, S.S. Yoon, Dyes Pigment 114, 40 (2015)

    Article  CAS  Google Scholar 

  21. T. Yu, W. Su, W. Li, Z. Hong, R. Hua, M. Li, B. Chu, B. Li, Z. Zhang, Z.Z. Hu, Inorg. Chim. Acta 359, 2246 (2006)

    Article  CAS  Google Scholar 

  22. T. Yu, W. Su, W. Li, Z. Hong, R. Hua, B. Li, Thin Solid Films 515, 4080 (2007)

    Article  CAS  Google Scholar 

  23. T. Yu, W. Su, W. Li, Z. Hong, R. Hua, M. Li, B. Chu, B. Li, Z. Zhang, Z.Z. Hu, Chem. Soc. Rev. 39, 189 (2010)

    Article  Google Scholar 

  24. V. Nishal, D. Singh, A. Kumar, V. Tanwar, I. Singh, R. Srivastava, P.S. Kadyan, J. Org. Semicond. 2, 15 (2014)

    Article  CAS  Google Scholar 

  25. V.B. Nagaveni, K.M. Mahadevan, G.R. Vijayakumar, H. Nagabhushana, S. Naveen, N.K. Lokanath, J. Sci. Adv. Mater. Dev. 3, 51 (2018)

    Google Scholar 

  26. C. Maxim, T.D. Pasatoiu, VCh. Kravtsov, S. Shova, C.A. Muryn, R.E.P. Winpenny, F. Tuna, M. Andruh, Inorg. Chim. Acta 361, 3903 (2008)

    Article  CAS  Google Scholar 

  27. M. Köse, G. Ceyhan, M. Tümer, I. Demirtas, I. Gönül, V. McKee, Spectrochim. Acta A 137, 477 (2015)

    Article  CAS  Google Scholar 

  28. J. Chakraborty, S. Thakurta, G. Pilet, R.F. Ziessel, L.J. Charbonnière, S. Mitra, Eur. J. Inorg. Chem. 26, 3993 (2009)

    Article  CAS  Google Scholar 

  29. L. He, L. Duan, J. Qiao, D. Zhang, G. Dong, L. Wang, Y. Qiu, Org. Electron. 10, 152 (2009)

    Article  CAS  Google Scholar 

  30. D. Sek, M. Siwy, K. Bijak, M. Filapek, G. Malecki, E.M. Nowak, J. Electroanal. Chem. 751, 128 (2015)

    Article  CAS  Google Scholar 

  31. Y. Niko, Y. Hiroshige, S. Kawauchi, G. Konishi, Tetrahedron 68, 6177 (2012)

    Article  CAS  Google Scholar 

  32. A. Gilbert, J. Bagott, Essentials of Molecular Photochemistry (CRC Press Boca Raton Inc., Florida, 1991)

    Google Scholar 

  33. H. Ishida, S. Tobita, Y. Hasegawa, R. Katoh, K. Nozaki, Coord. Chem. Rev. 254, 2449 (2010)

    Article  CAS  Google Scholar 

  34. E. Sarıpınar, C. Yılmaz, D. Unal, I.O. Ilhan, N. Yazır, Y. Akcamur, Hetero Cycles 68, 2045 (2006)

    Article  Google Scholar 

  35. Ü. Ceylan, M.E. Hacıyusufoğlu, S.P. Yalçın, M. Sönmez, M. Aygün, J. Mol. Struct. 1109, 209 (2016)

    Article  CAS  Google Scholar 

  36. A. Gencer Imer, R.H.B. Syan, M. Gülcan, Y.S. Ocak, A. Tombak, J. Mater. Sci.: Mater. Electron. 29, 898 (2017)

    Google Scholar 

  37. V.P. Singh, S. Singh, D.P. Singh, K. Tiwari, M. Mishra, J. Mol. Struct. 1058, 71 (2014)

    Article  CAS  Google Scholar 

  38. M. Gülcan, M. Sönmez, I. Berber, Turk. J. Chem. 36, 189 (2012)

    Google Scholar 

  39. M. Sönmez, M.E. Hacıyusufoğlu, Asian J. Chem. 18, 2032 (2006)

    Google Scholar 

  40. M. Sönmez, M. Çelebi, A. Levent, I. Berber, Z. Şentürk, J. Coord. Chem. 63, 848 (2010)

    Article  CAS  Google Scholar 

  41. S. Ilhan, H.M. Baykara, S. Seyitoglu, A. Levent, S. Özdemir, A. Dündar, A. Öztomsuk, M.H. Cornejo, J. Mol. Struct. 1075, 32 (2014)

    Article  CAS  Google Scholar 

  42. P. Zanello, Inorganic Electrochemistry; Theory, Practice and Application (The Royal Society of Chemistry, London, 2003)

    Google Scholar 

  43. M. Aguilar-Martinez, R. Saloma-Aguila, N. Macias-Ruvalcaba, R. Cetina-Rosado, A. Navarrete-Vazquez, V. Gomez-Vidales, A. Zantella-Dehesa, R.A. Toscano, S. Hernandez-Ortega, G.J.J. Fernandez, J. Chem. Soc., Dalton Trans. 16, 2327 (2001)

    Google Scholar 

  44. H. Kılıç, M. Berkem, J. Serb. Chem. Soc. 69, 689 (2004)

    Article  Google Scholar 

  45. M. Sönmez, M. Çelebi, A. Levent, I. Berber, Z. Şentürk, J. Coord. Chem. 63, 1986 (2010)

    Article  CAS  Google Scholar 

  46. S. Yaqiu, Y. Guangming, L. Daizheng, J. Zonghui, Y. Shiping, C. Peng, J. Mol. Struct. 842, 55 (2007)

    Article  CAS  Google Scholar 

  47. H. Liu, F.X. Li, Y. Pi, D.J. Wang, Y.J. Hu, J. Zheng, Spectrochim. Acta A 145, 588 (2015)

    Article  CAS  Google Scholar 

  48. M.K. Paul, Y.D. Singh, N.B. Singh, U. Sarkar, J. Mol. Struct. 1081, 316 (2015)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mehmet Sönmez.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 882 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sönmez, M., Hacıyusufoğlu, M.E., Levent, A. et al. Synthesis of pyrimidine Schiff base transition metal complexes: characterization, spectral and electrochemical analyses, and photoluminescence properties. Res Chem Intermed 44, 5531–5546 (2018). https://doi.org/10.1007/s11164-018-3438-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3438-5

Keywords

Navigation