Journal of the Iranian Chemical Society

, Volume 7, Issue 4, pp 825–833 | Cite as

Synthesis, crystal structure, electrochemical and fluorescence studies of a novel Zn(II)-fluorophore, 1,10-phenanthroline-5,6-dione (phen-dione)

Article

Abstract

The crystal structure of 1,10-phenanthroline-5,6-dione ligand with Zn(II), tris(1,10-phenanthroline-5,6-dione)zinc(II) hexafluorophosphate, [Zn(phen-dione)3](PF6)2, is reported. The complex was characterized by elemental analysis, IR, 1H NMR, electronic absorption spectroscopies, cyclic voltammetry and X-ray crystallography. Yellow crystals of [Zn(phen-dione)3](PF6)2 were formed by ether diffusion into an acetonitrile solution of the complex. The title complex crystallized in monoclinic crystal system (Z = 2) with space groups of P21, a = 12.0299(15) Å, b = 14.5306(19) Å, c = 13.1879(17) Å, β = 94.058(2)º and V = 2299.5(5) Å3. The structure was refined by using 10048 independent reflections, with I > 2σ(I) to an R factor of 0.0490. Single-crystal structure showed that the coordination geometry around the Zn(II) was a distorted octahedron. The complex showed an intense fluorescence band at visible region (690 nm) in CH3CN with an excitation wavelength of 310 nm at 25.0 ± 0.1 ºC.

Cyclic voltammogram of the title complex showed two quasi-reversible reduction couples at negative potential, which were assigned to the consecutive reduction of phen-dione ligand to phen-semiquinonate and phen-diolate respectively by analogy to other phen-dione complexes at scan rate 200 mV s-1.

Keywords

Zn(II) complex 1,10-Phenanthroline-5,6-dione Zn(II)-Fluorophore Phen-semiquinonate Fluorescence 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    F. Calderazzoz, G. Pampaloni, V. Passarelli, Inorg. Chim. Acta 330 (2002) 136.Google Scholar
  2. [2]
    U. Udeochu, T. Jimerson, A. Vivoni, O. Bakare, C.M. Hosten, J. Phys. Chem. A 111 (2007) 3409.Google Scholar
  3. [3]
    A.Y. Girgis, Y.S. Sohn, A.L. Balch, Inorg. Chem. 14 (1975) 2327.Google Scholar
  4. [4]
    M. Yamada, Y. Tanaka, Y. Yoshimoto, S. Kuroda, I. Shimao, Bull. Chem. Soc. Jpn. 65 (1992) 1006.Google Scholar
  5. [5]
    P.L. Hill, L.Y. Lee, T.R. Ypunkin, S.D. Orth, L. McElwee-White, Inorg. Chem. 36 (1997) 5655.Google Scholar
  6. [6]
    R.D. Gillard, R.E.E. Hill, R. Maskill, J. Chem. Soc. (1970) 1447.Google Scholar
  7. [7]
    S. Bodige, F.M. MacDonnell, Tetrahed. Lett. 38 (1997) 8159.Google Scholar
  8. [8]
    M.J. Kim, R. Konduri, H.W. Ye, F.M. MacDonnell, F. Rajeshwar, Inorg. Chem. 41 (2002) 2471.Google Scholar
  9. [9]
    K. Warnmark, J.A. Thomas, O. Heyke, J.M. Lehn, J. Chem. Soc., Chem. Commun. (1996) 701.Google Scholar
  10. [10]
    D.S. Sigman, A. Mazumder, D.M. Perrin. Chem. Rev. 93 (1993) 2295.Google Scholar
  11. [11]
    A. Sigl, H. Sigl (Eds.), Metal Ions in Biological System, Probing of Nucleic Acids by Metal Ion Complexes of Small Molecules, Vol. 33, Marcell Dekker, New York, 1996.Google Scholar
  12. [12]
    D.R. McMillin, K.M. McNett. Chem. Rev. 98 (1998) 1201.Google Scholar
  13. [13]
    S. Arounaguiri, B.G. Maiya, Inorg. Chem. 35 (1996) 4267.Google Scholar
  14. [14]
    K. Naing, M. Takashani, M. Taniguchi, A. Yamagishi, Inorg. Chem. 34 (1995) 350.Google Scholar
  15. [15]
    P.G. Sammes, G. Yahioglu, Chem. Soc. Rev. (1994) 327.Google Scholar
  16. [16]
    P.K. Bhattacharya, H.J. Lawson, J.K. Barton, Inorg. Chem. 42 (2003) 8811.Google Scholar
  17. [17]
    D.M. Boghaei, F. Behzadian Asl, Coord. Chem. 60 (2007) 1629.Google Scholar
  18. [18]
    P.K. Bhattacharya, H.J. Lawson, J.K. Barton, Inorg. Chem. 42 (2003) 8811.Google Scholar
  19. [19]
    M. Pascaly, J. Yoo, J.K. Barton, J. Am. Chem. Soc. 124 (2002) 9038.Google Scholar
  20. [20]
    N. Margiotta, V. Bertolasi, F. Capitelli, L. Maresca, A.G. Moliterni, F. Vizza, G. Natile, Inorg. Chim. Acta 357 (2004) 149.Google Scholar
  21. [21]
    P. Lenaerts, A. Torms, J. Mullens, J.D. Haen, C. Gorller-Waleand, K. Binnemans, K. Driesen, Chem. Mater. 17 (2005) 5194.Google Scholar
  22. [22]
    P.G. Sammes, G. Yahioglu, Chem. Soc. Rev. 23 (1994) 327.Google Scholar
  23. [23]
    T. Gennett, D.F. Milner, M.J. Weaver, J. Phys. Chem. 89 (1985) 787.Google Scholar
  24. [24]
    G.M. Sheldrick, SHELXS v. 5.1, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 1998.Google Scholar
  25. [25]
    R.S. Drago, Physical Methods for Chemists, Saunders College Publishing, New York, 1992, p. 118.Google Scholar
  26. [26]
    Z.-S. Peng, J.-X. Liu, W.-J. Jiang, Q. Deng, T.-J. Cai, M.-Z. Huan, NCS 223 (2008) 228.Google Scholar
  27. [27]
    C.A. Goss, H.D. Abruna, Inorg. Chem. 24 (1985) 4263.Google Scholar
  28. [28]
    H. Hadadzadeh, M.M. Olmsted, A.R. Rezvani, N. Safari, H. Saravani, Inorg. Chim. Acta 359 (2006) 2154.Google Scholar
  29. [29]
    K. Nakamato, Infrared and Raman Spectra of Inorganic and Coordination Compounds Part II: Application in Coordination, Organometallic and Bioinorganic Chemistry, 5th ed., Wiley-Interscience, New York, 1997.Google Scholar
  30. [30]
    G. Mansouri, A.R. Rezvani, H. Hadadzadeh, H.R. Khavasi, H. Saravani, J. Organomet. Chem. 692 (2007) 3810.Google Scholar
  31. [31]
    H. Saravani, A.R. Rezvani, G. Mansouri, A.R. Salehi Rad, H.R. Khavasi, H. Hadadzadeh, Inorg. Chim. Acta 360 (2007) 2829.Google Scholar
  32. [32]
    A.B.P. Lever, Inorganic Electronic Spectroscopy, 2nd ed., Elsevier, 1984.Google Scholar
  33. [33]
    S. Ikeda, S. Kimachi, T. Azumi, J. Phys. Chem. 100 (1996) 10528.Google Scholar
  34. [34]
    K. Kano, B. Uno, Anal. Chem. 65 (1993) 1088.Google Scholar
  35. [35]
    Y. Yamada, H. Sakurai, Y. Miyashita, K. Fujisawa, K. Okamoto, Polyhedron 21 (2002) 2143.Google Scholar
  36. [36]
    S. Berger, J. Fiedler, R. Reinhardt, W. Kaim, Inorg. Chem. 43 (2004) 1530.Google Scholar
  37. [37]
    V.W. Yam, Y.L. Pui, K. Kaicheung, Inorg. Chem. 39 (2000) 5741.Google Scholar
  38. [38]
    B.G. Maiya, Y. Deng, K.M. Kadish, J. Chem. Soc. Dalton Trans. (1990) 3571.Google Scholar
  39. [39]
    K.J. Nag, P.K. Santra, C. Sinha, F.L. Liao, T.H. Lu, Polyhedron 20 (2001) 2253.Google Scholar

Copyright information

© Iranian Chemical Society 2010

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of Sistan and BaluchestanZahedanIran
  2. 2.Department of ChemistryIsfahan University of TechnologyIsfahanIran

Personalised recommendations