Advertisement

Russian Chemical Bulletin

, Volume 68, Issue 2, pp 445–448 | Cite as

Synthesis and photophysical properties of 2,3,4,5-tetraphenyl-1-n-octyl-1-monophosphole

  • A. V. Petrov
  • A. A. ZagidullinEmail author
  • T. I. Burganov
  • N. I. Shatalova
  • S. A. Katsyuba
  • V. A. Milyukov
Brief Communications
  • 5 Downloads

Abstract

A new method for the preparation of 2,3,4,5-tetraphenyl-1-octyl-1-monophosphole was developed. It was shown that the reaction of n-octyl chloride with a mixture of sodium 1,2,3-tri-and 1-monophospholides obtained by refluxing sodium polyphosphides with diphenylacetylene resulted in the formation of exclusively 1-n-octyl-1-monophosphole. The photophysical properties of 1-n-octyl-1-monophosphole were studied by electron absorption and emission spectroscopy. According to the Raman spectroscopy data, the phenyl moieties of this molecule are efficiently conjugated with the diene system of the heterocycle leading to the appearance of the corresponding absorption and emission bands in the visible spectral range.

Key words

phosphorus heterocycles phosphole luminescence conjugation effects Raman spectroscopy 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    T. Baumgartner, R. Reau, Chem. Rev., 2006, 106, 4681.CrossRefGoogle Scholar
  2. 2.
    M. P. Duffy, W. Delaunay, P.-A. Bouit, M. Hissler, Chem. Soc. Rev., 2016, 45, 5296.CrossRefGoogle Scholar
  3. 3.
    M. Hissler, P. W. Dyer, R. Reau, Top. Curr. Chem., 2005, 250, 127.CrossRefGoogle Scholar
  4. 4.
    A. Zagidullin, I. A. Bezkishko, V. A. Miluykov, O. G. Sinyashin, Mendeleev. Commun., 2013, 23, 117.CrossRefGoogle Scholar
  5. 5.
    C. Hay, C. Fischmeister, M. Hissler, L. Toupet, R. Réau, Angew. Chem., Int. Ed. Engl., 2000, 39, 1812.CrossRefGoogle Scholar
  6. 6.
    C. Hay, C. Fave, M. Hissler, J. Rault-Berthelot, R. Reau, Org. Lett., 2003, 5, 3467.CrossRefGoogle Scholar
  7. 7.
    C. Fave, M. Hissler, T. Kárpáti, J. Rault-Berthelot, V. Deborde, L. Toupet, L. Nyulászi, R. Réau, J. Am. Chem. Soc., 2004, 126, 6058.CrossRefGoogle Scholar
  8. 8.
    C. Fave, T. Cho, M. Hissler, C. Chen, T. Luh, C. Wu, R. Réau, J. Am. Chem. Soc., 2003, 125, 9254.CrossRefGoogle Scholar
  9. 9.
    M. Hissler, C. Lescop, R. Reau, J. Organomet. Chem., 2005, 690, 2482.CrossRefGoogle Scholar
  10. 10.
    T. Baumgartner, Acc. Chem. Res., 2014, 47, 1613.CrossRefGoogle Scholar
  11. 11.
    M. Shameem, A. Orthaber, Chem. Eur. J., 2016, 22, 10718.CrossRefGoogle Scholar
  12. 12.
    E. Yamaguchi, C. Wang, A. Fukazawa, M. Taki, Y. Sato, T. Sasaki, M. Ueda, N. Sasaki, T. Hi-gashiyama, S. Yamaguchi, Angew. Chem., Int. Ed. Engl., 2015, 54, 4539.CrossRefGoogle Scholar
  13. 13.
    M. Taki, H. Ogasawara, H. Osaki, A. Fukazawa, Y. Sato, K. Ogasawara, T. Higashiyama, S. Yamaguchi, Chem. Commun., 2015, 51, 11880.CrossRefGoogle Scholar
  14. 14.
    X. He, P. Zhang, J.-B. Lin, H. V. Huynh, S. E. N. Muñ oz, C.-C. Ling, T. Baumgartner, Org. Lett., 2013, 15, 5322.CrossRefGoogle Scholar
  15. 15.
    K. Fourmy, D.H. Nguyen, O. Dechy-Cabaret, M. Gouygou, Catal. Sci. Technol., 2015, 5, 4289.CrossRefGoogle Scholar
  16. 16.
    M. Scheer, G. Balazs, A. Seitz, Chem. Rev., 2010, 110, 4236.CrossRefGoogle Scholar
  17. 17.
    V. A. Milykov, Y. H. Budnikova, O. G. Sinyashin, Russ. Chem. Rev., 2005, 74, 781.CrossRefGoogle Scholar
  18. 18.
    L. Xu, Y. Chi, S. Du, W. X. Zhang, Z. Xi, Angew. Chem., Int. Ed. Engl., 2016, 55, 9187.CrossRefGoogle Scholar
  19. 19.
    I. Bezkishko, A. Zagidullin, A. Petrov, V. Miluykov, O. Sinyashin, Phosphorus, Sulfur, Silicon Relat. Elem., 2016, 191, 1425.CrossRefGoogle Scholar
  20. 20.
    I. Bezkishko, V. Miluykov, A. Kataev, I. Litvinov, D. Krivolapov, O. Sinyashin, E. Hey-Hawkins, J. Organomet. Chem., 2008, 693, 3318.CrossRefGoogle Scholar
  21. 21.
    R. S. P. Turberville, J. M. Goicoechea, Chem. Commun., 2012, 48, 6100.CrossRefGoogle Scholar
  22. 22.
    I. A. Bezkishko, A. A. Zagidullin, V. A. Miluykov, O. G. Sinyashin, Russ. Chem. Rev., 2014, 83, 555.CrossRefGoogle Scholar
  23. 23.
    I. A. Bezkishko, A. A. Zagidullin, V. A. Miluykov, T. I. Burganov, S. A. Katsyuba, O. G. Sinyashin, J. Organomet. Chem., 2017, 844, 1.CrossRefGoogle Scholar
  24. 24.
    O. Fadhel, D. Szieberth, V. Deborde, C. Lescop, L. Nyulszi, M. Hissler, R. Reau, Chem. Eur. J., 2009, 15, 4914.CrossRefGoogle Scholar
  25. 25.
    I. A. Bezkishko, V. A. Miluykov, A. A. Zagidullin, O. G. Sinyashin, E. Hey-Hawkins, Russ. Chem. Bull., 2010, 59, 1232.CrossRefGoogle Scholar
  26. 26.
    D. Leung, S. O. Kang, E. V. Anslyn, Chem. Soc. Rev., 2012, 41, 448.CrossRefGoogle Scholar
  27. 27.
    L. Pu, Chem. Rev., 2004, 104, 1687.CrossRefGoogle Scholar
  28. 28.
    E. E. Zvereva, S. Grimme, S. A. Katsyuba, T. I. Burganov, A. A. Zagidullin, V. A. Milyukov, O. G. Sinyashin, J. Phys. Chem. A, 2013, 117, 6827.CrossRefGoogle Scholar
  29. 29.
    S. A. Katsyuba, T. I. Burganov, E. E. Zvereva, A. A. Zagidullin, V. A. Miluykov, P. Lö nnecke, E. Hey-Hawkins, O. G. Sinyashin, J. Phys. Chem. A, 2014, 118, 12168.CrossRefGoogle Scholar
  30. 30.
    T. Burganov, A. Zagidullin, E. Oshchepkova, S. Katsyuba, V. Miluykov, O. Sinyashin, Phosphorus, Sulfur, Silicon Relat. Elem., 2015, 190, 858.CrossRefGoogle Scholar
  31. 31.
    T. I. Burganov, S. A. Katsyuba, A. A. Zagidullin, E. E. Zvereva, V. A. Miluykov, O. G. Sinyashin, Russ. Chem. Bull., 2015, 64, 1896.CrossRefGoogle Scholar
  32. 32.
    S. A. Katsyuba, T. I. Burganov, Phosphorus, Sulfur, Silicon Relat. Elem., 2016, 191, 417.CrossRefGoogle Scholar
  33. 33.
    T. I. Burganov, A. A. Zagidullin, S. A. Katsyuba, V. A. Miluykov, O. G. Sinyashin, Phosphorus, Sulfur, Silicon Relat. Elem., 2016, 191, 1646.CrossRefGoogle Scholar
  34. 34.
    A. Zagidullin, E. Oshchepkova, T. Burganov, V. Miluykov, S. Katsyuba, O. Sinyashin, P. Lönnecke, E. Hey-Hawkins, J. Organomet. Chem., 2017, 867, 125.CrossRefGoogle Scholar
  35. 35.
    E. Oshchepkova, A. Zagidullin, T. Burganov, S. Katsyuba, V. Miluykov, O. Lodochnikova, Dalton Trans., 2018, 47, 11521.CrossRefGoogle Scholar
  36. 36.
    M. V. Vol´kenshtein, Zh. Fiz. Khim., 1943, 17, 367 [Russ. J. Phys. Chem. (Engl. Transl.), 1943, 17].Google Scholar
  37. 37.
    P. P. Shorygin, Zh. Fiz. Khim., 1947, 21, 1125 [Russ. J. Phys. Chem. (Engl. Transl.), 1947, 21].Google Scholar
  38. 38.
    P. P. Shorygin, Usp. Khim., 1971, 15, 694 [Russ. Chem. Rev., 1971, 15].Google Scholar
  39. 39.
    L. A. Leites, S. S. Bukalov, J. Raman Spectrosc., 2001, 32, 413.CrossRefGoogle Scholar
  40. 40.
    E. D. Schmid, R. D. Topsom, J. Am. Chem. Soc., 1981, 103, 1628.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  • A. V. Petrov
    • 1
  • A. A. Zagidullin
    • 1
    Email author
  • T. I. Burganov
    • 1
  • N. I. Shatalova
    • 2
  • S. A. Katsyuba
    • 1
  • V. A. Milyukov
    • 1
  1. 1.A. E. Arbuzov Institute of Organic and Physical ChemistryFederal Research Center “Kazan Scientific Center of the Russian Academy of Sciences,”KazanRussian Federation
  2. 2.Kazan National Research Technological UniversityKazanRussian Federation

Personalised recommendations