Synthesis, characterization, and photoluminescence properties of difluoroboron complexes with bis-β-diketone ligands

Abstract

Some novel difluoroboron bis-β-diketonates containing a pyridyl moiety were synthesized from diethyl 2,6-pyridinedicarboxylate via Claisen condensation with the corresponding aryl methyl ketones and followed by complexation with boron trifluoride etherate. Their spectroscopic behaviors were studied by FTIR, 1H NMR, UV–Vis, and fluorescence spectroscopic techniques. The results indicated that difluoroboron bis-β-diketonates exhibited violet or blue fluorescence emission at 428–454 nm under UV illumination in DMSO and possessed high extinction coefficients. It was found that the nature of the substituents at benzene ring in bis-β-diketone ligands had a significant impact on the photoluminescence behaviors of difluoroboron complexes. The complex 5b exhibited the strongest photoluminescence intensity and highest quantum yield (Φ u = 0.93), due to two strong electron-donating methoxyl moieties in molecule and the compound 4b displayed the lowest photoluminescence intensity and quantum yield, assigned to the heavy atom effect of the chlorine atom in its molecule. The photoluminescence intensity and quantum yield of these difluoroboron complexes decreased in the sequence, 5b > 2b > 1b > 3b > 4b.

This is a preview of subscription content, access via your institution.

We’re sorry, something doesn't seem to be working properly.

Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Scheme 1
Fig. 1
Fig. 2

References

  1. 1.

    W. Dilthey, F. Eduardoff, F.J. Schumacher, J. Liebigs Ann. Chem. 344, 300–313 (1906)

    CAS  Article  Google Scholar 

  2. 2.

    M.J. Mayoral, P. Ovejero, M. Cano, G. Orellana, Dalton Trans. 40, 377–383 (2011)

    CAS  Article  Google Scholar 

  3. 3.

    E. Cogné-Laage, J.-F. Allemand, O. Ruel, J.-B. Baudin, V. Croquette, M. Blanchard-Desce, L. Julien, Chem. Eur. J. 10, 1445–1455 (2004)

    Article  Google Scholar 

  4. 4.

    K. Ono, K. Yoshikawa, Y. Tsuji, H. Yamaguchi, R. Uozumi, M. Tomura, K. Taga, K. Saito, Tetrahedron 63, 9354–9358 (2007)

    CAS  Article  Google Scholar 

  5. 5.

    A.V. Nyuchev, K.V. Schegravin, M.A. Lopatin, V.V. Fokin, I.P. Beletskaya, A.Y. Fedorov, Synthesis 46, 3239–3248 (2014)

    CAS  Article  Google Scholar 

  6. 6.

    S. Xu, R.E. Evans, T. Liu, G. Zhang, J.N. Demas, C.O. Trindle, C.L. Fraser, Inorg. Chem. 52, 3597–3610 (2013)

    CAS  Article  Google Scholar 

  7. 7.

    L.A. Padilha, S. Webster, O.V. Przhonska, H. Hu, D. Peceli, T.R. Ensley, M.V. Bondar, A.O. Gerasov, Y.P. Kovtun, M.P. Shandura, A.D. Kachkovski, D.J. Hagan, E.W.V. Stryland, J. Phys. Chem. A 114, 6493–6501 (2010)

    CAS  Article  Google Scholar 

  8. 8.

    E.V. Fedorenko, A.G. Mirochnik, I.B. Lvov, V.I. Vovna, Spectrochim. Acta Part A 120, 119–125 (2014)

    CAS  Article  Google Scholar 

  9. 9.

    Y. Sun, D. Rohde, Y. Liu, L. Wan, Y. Wang, W. Wu, C. Di, G. Yu, D. Zhu, J. Mater. Chem. 16, 4499–4503 (2006)

    CAS  Article  Google Scholar 

  10. 10.

    C. Ran, X. Xu, S.B. Raymond, B.J. Ferrara, K. Neal, B.J. Bacskai, Z. Medarova, A. Moore, J. Am. Chem. Soc. 131, 15257–15261 (2009)

    CAS  Article  Google Scholar 

  11. 11.

    G. Bai, C. Yu, C. Cheng, E. Hao, Y. Wei, X. Mu, L. Jiao, Org. Biomol. Chem. 12, 1618–1626 (2014)

    CAS  Article  Google Scholar 

  12. 12.

    E. Giziroglu, A. Nesrullajev, N. Orhan, J. Mol. Struct. 1056–1057, 246–253 (2014)

    Article  Google Scholar 

  13. 13.

    E.V. Fedorenko, A.G. Mirochnik, A.Y. Beloliptsev, V.V. Isakov, Dyes Pigments 109, 181–188 (2014)

    CAS  Article  Google Scholar 

  14. 14.

    A. D’Aléo, A. Felouat, F. Fages, Adv. Nat. Sci. Nanosci. Nanotechnol. 6, 015009 (2015)

    Article  Google Scholar 

  15. 15.

    B. Domercq, C. Grasso, J.-L. Maldonado, M. Halik, S. Barlow, S.R. Marder, B. Kippelen, J. Phys. Chem. B 108, 8647–8651 (2004)

    CAS  Article  Google Scholar 

  16. 16.

    Y. Pi, D.-J. Wang, H. Liu, Y.-J. Hu, X.-H. Wei, J. Zheng, Spectrochim. Acta Part A 131, 209–213 (2014)

    CAS  Article  Google Scholar 

  17. 17.

    D.-J. Wang, Y.-F. Kang, L. Fan, Y.-J. Hu, J. Zheng, Opt. Mater. 36, 357–361 (2013)

    CAS  Article  Google Scholar 

  18. 18.

    J.N. Demas, G.A. Crosby, J. Phys. Chem. 75, 991–1024 (1971)

    Article  Google Scholar 

  19. 19.

    B.-P. Xu, Y.-F. Kang, D.-J. Wang, J.-J. Shang, Q. Wei, J. Hubei Normal Univ. Nat. Sci. 32, 75–77 (2012). (in Chinese)

    Google Scholar 

  20. 20.

    V.A. Reutov, E.V. Gukhman, E.E. Kafitulova, Russ. J. Gen. Chem. 73, 1441–1444 (2003)

    CAS  Article  Google Scholar 

  21. 21.

    N.M.D. Brown, P. Bladon, J. Chem. Soc. A, 526–532 (1969)

  22. 22.

    I.V. Svistunova, E.V. Fedorenko, Russ. J. Gen. Chem. 78, 1515–1523 (2008)

    CAS  Article  Google Scholar 

  23. 23.

    V.V. Osipov, M.N. Usacheva, I.I. Dilung, Zh. Prikl. Spektrosk. 39, 637–641 (1984)

    Google Scholar 

Download references

Acknowledgments

The authors would like to acknowledge the support from National Natural Science Foundation of China (No. 21273065) and the Educational Commission of Hubei Province (No. B2015132).

Author information

Affiliations

Authors

Corresponding author

Correspondence to Dun-Jia Wang.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Liu, H., Yang, JH., Lin, L. et al. Synthesis, characterization, and photoluminescence properties of difluoroboron complexes with bis-β-diketone ligands. Res Chem Intermed 42, 2857–2866 (2016). https://doi.org/10.1007/s11164-015-2182-3

Download citation

Keywords

  • Difluoroboron complexes
  • Bis-β-diketone
  • Photoluminescence
  • Quantum yield
  • Spectroscopic properties