Research on Chemical Intermediates

, Volume 45, Issue 4, pp 1669–1687 | Cite as

Synthesis and photophysical properties of europium pentafluorinated β-diketonate complexes

  • Yupeng Wan
  • Heng Lyu
  • Hengyi Du
  • Dunjia WangEmail author
  • Guodong Yin


Two pentafluorinated β-diketone ligands, 4,4,5,5,5-pentafluoro-1-(4-methoxyphenyl)pentane-1,3-dione (PFMP) and 4,4,5,5,5-pentafluoro-1-(4-dimethyl amino-phenyl)pentane-1,3-dione (PFAP), had been employed to synthesize six novel europium (III) complexes with ancillary ligands 2,2-dipyridine, 1,10-phenanthroline and 4,7-diphenyl-1,10-phenanthroline. The synthesized europium (III) complexes were characterized by FTIR, 1H NMR, UV–Vis, luminescence spectroscopy, elemental analysis and thermogravimetric analysis. The photoluminescence spectra of these complexes showed the typical europium (III) red emissions in solid state and chloroform solution, assigned to 5D0 → 7Fj (j = 0–4) transitions. The higher values of intensity parameter Ω2 indicated that the europium ion was in a highly polarizable ligand field in these complexes. Europium (III) complexes with the β-diketone PFMP exhibited much better photoluminescence properties than complexes with the β-diketone PFAP. Especially, the europium (III) complex of the β-diketone PFMP with the auxiliary ligand 2,2-dipyridine displayed the longest lifetime value, the highest quantum yield and good CIE color coordinates matching the pure red color (x = 0.67, y = 0.33) in these complexes. In addition, the proposed energy transfer mechanisms and the thermal stability of these complexes were also investigated and analyzed.


Europium complex Pentafluorinated β-diketone Photoluminescence Quantum efficiency Luminescent lifetime Thermal analysis 



The authors gratefully acknowledge financial support from National Natural Science Foundation of China (No. 21542009) and Foundation for Hubei Key Laboratory of Pollutant Analysis and Reuse Technology (No. PA160203).

Supplementary material

11164_2018_3691_MOESM1_ESM.doc (700 kb)
Supplementary material 1 (DOC 700 kb)


  1. 1.
    M.L. Di Lorenzo, M. Cocca, G. Gentile, M. Avella, D. Gutierrez, M.D. Pirriera, M. Kennedy, H. Ahmed, J. Doran, J. Colloid Interface Sci. 398, 95 (2013)CrossRefGoogle Scholar
  2. 2.
    P. Shukla, V. Sudarsan, R.K. Vatsa, S.K. Nayak, S. Chattopadhyay, J. Lumin. 130, 1952 (2010)CrossRefGoogle Scholar
  3. 3.
    F.-B. Wu, C. Zhang, Anal. Biochem. 311, 57 (2002)CrossRefGoogle Scholar
  4. 4.
    M.H.V. Werts, R.T.F. Jukes, J.W. Verhoeven, Phys. Chem. Chem. Phys. 4, 1542 (2002)CrossRefGoogle Scholar
  5. 5.
    G.F. De Sá, O.L. Malta, C. de Mello Donegá, A.M. Simas, R.L. Longo, P.A. Santa-Cruz, E.F. Da Silva Jr., Coord. Chem. Rev. 196, 165 (2000)CrossRefGoogle Scholar
  6. 6.
    H. Iwanaga, J. Lumin. 200, 233 (2018)CrossRefGoogle Scholar
  7. 7.
    Y.H. Pham, V.A. Trush, V.M. Amirkhanov, P. Gawryszewska, Opt. Mater. 74, 197 (2017)CrossRefGoogle Scholar
  8. 8.
    J.P. Martins, P. Martín-Ramos, C. Coya, M.R. Silva, M.E.S. Eusebio, A. de Andrés, Á.L. Álvarez, J. Martín-Gil, J. Lumin. 159, 17 (2015)CrossRefGoogle Scholar
  9. 9.
    C. Yang, J. Xu, J. Ma, D. Zhu, Y. Zhang, L. Liang, M. Lu, Polym. Chem. 3, 2640 (2012)CrossRefGoogle Scholar
  10. 10.
    Y. Wang, H. Wang, X. Zhao, Y. Jin, H. Xiong, J. Yuan, J. Wu, New J. Chem. 41, 5981 (2017)CrossRefGoogle Scholar
  11. 11.
    K. Kuriki, Y. Koike, Y. Okamoto, Chem. Rev. 102, 2347 (2002)CrossRefGoogle Scholar
  12. 12.
    B. Rajamouli, S. Kasturi, S. Giri, V. Sivakumar, Inorg. Chem. 56, 10127 (2017)CrossRefGoogle Scholar
  13. 13.
    B. Rajamouli, C.S.D. Viswanath, S. Giri, C.K. Jayasankar, V. Sivakumar, New J. Chem. 41, 3112 (2017)CrossRefGoogle Scholar
  14. 14.
    D.B. Ambili Raj, S. Biju, M.L.P. Reddy, Dalton Trans. 36, 7519 (2009)CrossRefGoogle Scholar
  15. 15.
    R. Devi, M. Bala, S.P. Khatkar, V.B. Taxak, P. Boora, J. Fluor. Chem. 181, 36 (2016)CrossRefGoogle Scholar
  16. 16.
    X. Zhao, Z. Hou, B. Wang, Q. Shen, H. Jia, A. Zhang, X. Liu, B. Xu, Res. Chem. Intermed. 43, 4129 (2017)CrossRefGoogle Scholar
  17. 17.
    B. Rajamouli, P. Sood, S. Giri, V. Krishnan, V. Sivakumar, Eur. J. Inorg. Chem. 24, 3900 (2016)CrossRefGoogle Scholar
  18. 18.
    S. Kasturi, B. Rajamouli, V. Sivakumar, Inorg. Chem. 56, 9376 (2017)CrossRefGoogle Scholar
  19. 19.
    B. Rajamouli, V. Sivakumar, ChemistrySelect 2, 4138 (2017)CrossRefGoogle Scholar
  20. 20.
    B. Rajamouli, V. Sivakumar, J. Photochem. Photoboil. A 347, 26 (2017)CrossRefGoogle Scholar
  21. 21.
    D. Wang, Y. Pi, H. Liu, X. Wei, Y. Hu, J. Zheng, J. Alloys Compd. 613, 13 (2014)CrossRefGoogle Scholar
  22. 22.
    D. Wang, H. Liu, L. Fan, G. Yin, Y. Hu, J. Zheng, Synth. Met. 209, 267 (2015)CrossRefGoogle Scholar
  23. 23.
    D. Wang, C. Zheng, L. Fan, Y. Hu, J. Zheng, Spectrochim. Acta Part A 117, 245 (2014)CrossRefGoogle Scholar
  24. 24.
    D.B. Ambili Raj, S. Biju, M.L.P. Reddy, Inorg. Chem. 47, 8091 (2008)CrossRefGoogle Scholar
  25. 25.
    B. Francis, D.B. Ambili Raj, M.L.P. Reddy, Dalton Trans. 39, 8084 (2010)CrossRefGoogle Scholar
  26. 26.
    D.B. Ambili Raj, B. Francis, M.L.P. Reddy, R.R. Butorac, V.M. Lynch, A.H. Cowley, Inorg. Chem. 49, 9055 (2010)CrossRefGoogle Scholar
  27. 27.
    V. Divya, M.L.P. Reddy, J. Mater. Chem. C 1, 160 (2013)CrossRefGoogle Scholar
  28. 28.
    J.N. Demas, G.A. Crosby, J. Phys. Chem. 75, 991 (1971)CrossRefGoogle Scholar
  29. 29.
    C. Yang, J. Luo, J. Ma, M. Lu, L. Liang, B. Tong, Dyes Pigments 92, 696 (2011)CrossRefGoogle Scholar
  30. 30.
    L.R. Melby, N.J. Rose, E. Abramson, J.C. Caris, J. Am. Chem. Soc. 86, 5117 (1964)CrossRefGoogle Scholar
  31. 31.
    Y. Zhang, H. Shi, Y. Ke, Y. Cao, J. Lumin. 124, 51 (2007)CrossRefGoogle Scholar
  32. 32.
    L. Fu, R.A.S. Ferreira, N.J.O. Silva, A.J. Fernandes, P. Ribeiro-Claro, I.S. Goncalves, V. de Zea Bermudez, L.D. Carlos, J. Mater. Chem. 15, 3117 (2005)CrossRefGoogle Scholar
  33. 33.
    N.S. Bhacca, J. Selbin, J.D. Wander, J. Am. Chem. Soc. 94, 8719 (1972)CrossRefGoogle Scholar
  34. 34.
    K. Iftikhar, Polyhedron 15, 1113 (1996)CrossRefGoogle Scholar
  35. 35.
    V. Sareen, R. Gupta, J. Fluor. Chem. 76, 149 (1996)CrossRefGoogle Scholar
  36. 36.
    X. Jiang, Y. Wu, C. He, Mater. Lett. 62, 286 (2008)CrossRefGoogle Scholar
  37. 37.
    K. Nakamoto, Infrared and Raman Spectra of Inoganic and Coordination Compounds, 6th edn. (Wiley, New Jersey, 2009), p. 23Google Scholar
  38. 38.
    M.C.F.C. Felinto, C.S. Tomiyama, H.F. Brito, E.E.S. Teotonio, O.L. Malta, J. Solid State Chem. 171, 189 (2003)CrossRefGoogle Scholar
  39. 39.
    O.L. Malta, H.F. Brito, J.F.S. Menezes, F.R.G. e Silva, S. Alves Jr., F.S. Farias Jr., A.V.M. de Andrade, J. Lumin. 75, 255 (1997)CrossRefGoogle Scholar
  40. 40.
    P. He, H. Wang, S. Liu, W. Hu, J. Shi, G. Wang, M. Gong, J. Electrochem. Soc. 156, E46 (2009)CrossRefGoogle Scholar
  41. 41.
    A. Beeby, I.M. Clarkson, R.S. Dickins, S. Faulkner, D. Parker, L. Royle, A.S. de Sousa, J.A.G. Williams, S.M. Wood, J. Chem. Soc. Perkin Trans. 2, 493 (1999)CrossRefGoogle Scholar
  42. 42.
    J.R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd edn. (Springer, New York, 2006), p. 99CrossRefGoogle Scholar
  43. 43.
    R. Ferreira, P. Pires, B. de Castro, R.A.S. Ferreira, L.D. Carlos, U. Pischel, New J. Chem. 28, 1506 (2004)CrossRefGoogle Scholar
  44. 44.
    D. Wang, Z. Luo, Z. Liu, D. Wang, L. Fan, G. Yin, Dyes Pigments 132, 398 (2016)CrossRefGoogle Scholar
  45. 45.
    R. Devi, Priyanka, S. Chahar, S.P. Khatkar, V.B. Taxak, P. Boora, Inorg. Chim. Acta 471, 364 (2018)CrossRefGoogle Scholar
  46. 46.
    M.O. Rodrigues, N.B. da Costa Júnior, C.A. de Simone, A.A.S. Araújo, A.M. Brito-Silva, F.A. Almeida Paz, M.E. de Mesquita, S.A. Júnior, R.O. Freire, J. Phys. Chem. B 112, 4204 (2008)CrossRefGoogle Scholar
  47. 47.
    A.A.S. Araújo, H.F. Brito, O.L. Malta, J.R. Matos, E.E.S. Teotonio, S. Storpirtis, C.M.S. Izumi, J. Inorg. Biochem. 88, 87 (2002)CrossRefGoogle Scholar
  48. 48.
    M. Latva, H. Takalo, V.M. Mukkala, C. Matachescu, J.C. Rodriguez-Ubis, J. Kankare, J. Lumin. 75, 149 (1997)CrossRefGoogle Scholar
  49. 49.
    F.J. Steemers, W. Verboom, D.N. Reinhoudt, E.B. van der Tol, J.W. Verhoeven, J. Am. Chem. Soc. 117, 9408 (1995)CrossRefGoogle Scholar
  50. 50.
    R. Devi, M. Dalal, M. Bala, S.P. Khatkar, V.B. Taxak, P. Boora, J. Mater. Sci. Mater. Electron. 27, 12506 (2016)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Yupeng Wan
    • 1
  • Heng Lyu
    • 1
  • Hengyi Du
    • 1
  • Dunjia Wang
    • 1
    Email author
  • Guodong Yin
    • 1
  1. 1.College of Chemistry and Chemical Engineering, Hubei Key Laboratory of Pollutant Analysis and Reuse TechnologyHubei Normal UniversityHuangshiChina

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