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Synthesis, spectral and thermal properties of some transition metal(II) complexes with a novel ligand derived from thiobarbituric acid

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Abstract

Four novel metal(II) complexes, Ni(L)2, Co(L)2, Cu(L)2, and Zn(L)2 (L = 5-(2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)hydrazono)-1,3-diethyl-2-thioxo-dihydropyrimidine-4,6(1H,5H)-dione), were synthesized using the procedure of diazotization, coupling and metallization. Their structures were identified by elemental analyses, 1H NMR, ESI-MS and FT-IR spectra. The effect of different central metal(II) ions on absorption bands of the metal(II) complexes was researched. The thermal properties of the metal(II) complexes were investigated by thermogravimetry (TG) and differential scanning calorimetry (DSC). Furthermore, the thermodynamic parameters, such as activation energy (E*), enthalpy (∆H*), entropy (∆S*) and free energy of the decomposition (∆G*) are calculated from the TG curves applying Coats–Redfern method. The results show that the metal(II) complexes have suitable electronic absorption spectra with blue-violet light absorption at about 350–450 nm, high thermal stability with sharp thermal decomposition thresholds.

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References

  1. Kuwahara M, Takehara S, Kashihara Y, Watabe K, Nakano T, Tanaka M, et al. Experimental study of high-density rewritable optical disk using a blue-laser diode. Jpn J Appl Phys. 2003;42:1068–71.

    Article  CAS  Google Scholar 

  2. Chang D, Yoon D, Ro M, Park I, Shin D. Synthesis and characteristics of protective coating on thin cover layer for high density-digital versatile disc. Jpn J Appl Phys. 2003;42:754–8.

    Article  CAS  Google Scholar 

  3. Huang FX, Wu YQ, Gu DH, Gan FX. Spectroscopic and thermal properties of short wavelength metal (II) complexes containing α-isoxazolylazo-β-diketones as co-ligands. Spectrochim Acta A. 2005;61:2856–60.

    Article  Google Scholar 

  4. Park H, Kim ER, Kim DJ, Lee H. Synthesis of metal-azo dyes and their optical and thermal properties as recording materials for DVD-R. Bull Chem Soc Jpn. 2002;75:2067–70.

    Article  CAS  Google Scholar 

  5. Chen ZM, Wu YQ, Gu DH, Gan FX. Nickel(II) and copper(II) complexes containing 2-(2-(5-substitued isoxazol-3-yl)hydrazono)-5,5-dimethylcyclohexane- 1,3-dione ligands: synthesis, spectral and thermal characterizations. Dye Pigment. 2008;76:624–31.

    Article  CAS  Google Scholar 

  6. Wang S, Shen S, Xu H. Synthesis, spectroscopic and thermal properties of a series of azo metal chelate dyes. Dye Pigment. 2000;44:195–8.

    Article  CAS  Google Scholar 

  7. Wu SJ, Qian W, Xia ZJ, Zou YH, Wang SQ, Shen SY, et al. Investigation of third-order nonlinearity of an azo dye and its metal-substituted compounds. Chem Phys Lett. 2000;330:535–40.

    Article  CAS  Google Scholar 

  8. Abe T, Mano S, Yamada Y, Tomotake A. Thermal dye transfer printing with chelate compounds. J Imaging Sci Technol. 1999;43:339–44.

    CAS  Google Scholar 

  9. Gup R, Gizioglu E, Kırkan B. Synthesis and spectroscopic properties of new azo-dyes and azo-metal complexes derived from barbituric acid and aminoquinoline. Dye Pigment. 2007;73:40–6.

    Article  CAS  Google Scholar 

  10. Karcı F, Karcı F. The synthesis and solvatochromic properties of some novel heterocyclic disazo dyes derived from barbituric acid. Dye Pigment. 2008;77:451–6.

    Article  Google Scholar 

  11. Song HF, Chen KC, Tian H. Synthesis of novel dyes derived from 1-ethyl-3-cyano-6-hydroxy-4-methyl-5-amino-2-pyridone. Dye Pigment. 2002;53:257–62.

    Article  CAS  Google Scholar 

  12. Kirkan B, Gup R. Synthesis of new azo dyes and Copper(II) complexes derived from barbituric acid and 4-aminobenzoylhydrazone. Turk J Chem. 2008;32:9–17.

    CAS  Google Scholar 

  13. Christie RM, Dryburgh WT, Standring PN. Some monoazoacetoacetanilide pigments derived from heterocyclic diazo components. Dye Pigment. 1991;16:231–40.

    Article  CAS  Google Scholar 

  14. El-Boraey HA, El-Saied FA, Aly SA. UO2(VI), Sn(IV), Th(IV) and Li(I) complexes of 4-azomalononitrile antipyrine. J Therm Anal Calorim 2009;96:599–606. doi:10.1007/s10973-008-9197-6.

  15. Karcı F, Karcı F. Synthesis and absorption spectra of some novel heterocyclic disazo dyes derived from pyridone and pyrazolone derivatives. Dye Pigment. 2008;76:147–57.

    Article  Google Scholar 

  16. Ertan N, Gürkan P. Synthesis and properties of some azo pyridone dyes and their Cu(II) complexes. Dye Pigment. 1997;33:137–47.

    Article  CAS  Google Scholar 

  17. Peng Q, Li M, Gao K, Cheng L. Hydrazone-azo tautomerism of pyridone azo dyes: Part 1—NMR Spectra of Tautomers. Dye Pigment. 1990;14:89–99.

    Article  CAS  Google Scholar 

  18. Bâtiu C, Panea I, Ghizdavu L, David L, Ghizdavu Pellascio S. Divalent transition metal complexes 4-(4-ethoxy-phenylhydrazono)-1-phenyl-3-methyl-1H-pyrazolin-5 (4H)-one . J Therm Anal Calorim. 2005;79:129–34.

    Article  Google Scholar 

  19. Peng Q, Li M, Gao K, Cheng L. Hydrazone-azo tautomerism of pyridone azo dyes: Part III—effect of dye structure and solvents on the dissociation of pyridone azo dyes. Dye Pigment. 1992;18:271–86.

    Article  CAS  Google Scholar 

  20. Issa RM, Khedr AM, Rizk HF. UV–vis, IR and 1H NMR spectroscopic studies of some Schiff bases derivatives of 4-aminoantipyrine. Spectrochim Acta A. 2005;62:621–9.

    Article  Google Scholar 

  21. Ropret P, Centeno SA, Bukovec P. Raman identification of yellow synthetic organic pigments in modern and contemporary paintings: reference spectra and case studies. Spectrochim Acta A. 2008;69:486–97.

    Article  Google Scholar 

  22. Abdel-Latif SA, Hassib HB. Studies of Mn(II), Co(II), Ni(II) and Cu(II) Chelates with 3-phenyl-4-(p-methoxy-phenylazo)-5-pyrazolone. J Therm Anal Calorim. 2002;68:983–95.

    Article  CAS  Google Scholar 

  23. Garg BS, Sharma RK, Kundra E. Copper(II), nickel(II), cobalt(II) and zinc(II) complexes of 2-[2-(6-methylbenzothiazolyl)azo]-5-dimethylaminobenzoic acid: synthesis, spectral, thermal and molecular modelling studies. Transition Met Chem. 2005;30:552–9.

    Article  CAS  Google Scholar 

  24. Omar MM, Mohamed GG. Potentiometric, spectroscopic and thermal studies on the metal chelates of 1-(2-thiazolylazo)-2-naphthalenol. Spectrochim Acta A. 2005;61:929–36.

    Article  CAS  Google Scholar 

  25. Xu G-C, Zhang L, Liu L, Liu G-F, Jia D-Z. Kinetics of thermal decomposition of mixed-ligand nikkel(II) and copper(II) complexes of 4-acyl pyrazolone derivative and pyridine. J Therm Anal Calorim. 2007;89:547–53.

    Article  CAS  Google Scholar 

  26. Griffiths J, Translated by Hou YF, Wu ZW, Hu JZ. Colour and constitution of organic molecules. Beijing: Chemistry Industry Press; 1985. p. 202.

  27. Snavely FA, Suydam FH. Notes- structure of aryl azo pyrozolone compounds and their copper derivatives. J Org Chem. 1959;24:2039–40.

    Article  CAS  Google Scholar 

  28. Zaitev BE, Zaiteva VA, Molodkin AK, Obraztova ES. Synthesis and the structure of 1-phenyl-3-methyl-4-phenylazopyrazol-5-one with Cu(ІІ) and Co(ІІ). Zh Neorg Khim. 1979;24:127–33.

    Google Scholar 

  29. Coat AW, Redfern JP. Kinetic parameters from thermogravimetric data. Nature. 1964;201:68–9.

    Article  Google Scholar 

  30. Kandil SS, El-Hefnawy GB, Baker EA. Thermal and spectral studies of 5-(phenylazo)-2-thiohydantoin and 5-(2-hydroxyphenylazo)-2-thiohydantoin complexes of cobalt(II), nickel(II) and copper(II). Thermochim Acta. 2004;414:105–13.

    Article  CAS  Google Scholar 

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Acknowledgements

Financial support from the National Natural Science Foundation of China (No. 60490290), Chinese Academy of Sciences (KJCX2.YW.M06) and the National Science and Technology Program of China (No. 2007AA03Z412) is gratefully acknowledged.

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Correspondence to Yiqun Wu.

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Li, X., Wu, Y., Gu, D. et al. Synthesis, spectral and thermal properties of some transition metal(II) complexes with a novel ligand derived from thiobarbituric acid. J Therm Anal Calorim 98, 387–394 (2009). https://doi.org/10.1007/s10973-009-0290-2

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  • DOI: https://doi.org/10.1007/s10973-009-0290-2

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