Advertisement

Russian Chemical Bulletin

, Volume 64, Issue 8, pp 1933–1941 | Cite as

Reactivity of phthalocyanine precursors

  • A. V. Lyubimtsev
  • N. V. Zheglova
  • E. N. Smirnova
  • S. A. Syrbu
Full Articles

Abstract

A higher reactivity of 4-nitrophthalonitrile as compared to phthalonitrile and 4-amino-phthalonitrile in the reaction with sodium methoxide in methanol was demonstrated by theoretical (semiempirical, ab initio calculations) and experimental methods. The regioisomeric composition of substituted methoxyiminoisoindolenines was studied by analysis of products of their reaction with p-toluidine. The higher reactivity of 3-imino-1-methoxyisoindolenine as compared to 1,3-diiminoisoindoline in the reactions with nucleophilic agents (ammonia, p-toluidine) was shown by semiempirical calculations and kinetic methods.

Key words

phthalonitrile 4-nitrophthalonitrile 4-aminophthalonitrile reactivity 3-imino-1-methoxyisoindolenine 1,3-diiminoisoindoline semiempirical and ab initio quantum chemical calculations density functional theory functional B3LYP 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    ICI GB Pat. 464 126, 1937; http://worldwide.espacenet.com.Google Scholar
  2. 2.
    P. Erk, H. Engelsberg, in The Porphyrin Handbook, Eds K. M. Kadish, K. M. Smith, R. Guilard, Elsevier Science, San Diego, 2003, Vol. 19, 105.Google Scholar
  3. 3.
    G. Löbbert, Phthalocyanines, Ullmann´s Encyclopedia of Industrial Chemistry, Vol. A20, VCH Publ., Weinheim, 1992, p. 213Google Scholar
  4. 3a.
    D. Wöhrle, G. Schnurpfeil, S. Makarov, O. Suvorova, Chem. Unserer Zeit, 2012, 46, 12.CrossRefGoogle Scholar
  5. 4.
    H. E. Katz, Z. Bao, S. L. Gilat, Acc. Chem. Res., 2001, 34, 359.CrossRefGoogle Scholar
  6. 5.
    Q. Tang, H. Li, M. He, W. Hu, C. Liu, K. Chen, C. Wang, Y. Liu, D. Zhu, Adv. Mater., 2006, 18, 65.CrossRefGoogle Scholar
  7. 6.
    K. S. Karimov, I. Qazi, T. A. Khan, P. H. Draper, F. A. Khalid, M. Mahroof-Tahir, Environ Monit Assess, 2008, 141, 323.CrossRefGoogle Scholar
  8. 7.
    M. Bouvet, Anal. Bioanal. Chem., 2006, 384, 366.CrossRefGoogle Scholar
  9. 8.
    A. Cole, R. J. McIlroy, S. C. Thorpe, M. J. Cook, J. McMurdo, A. K. Ray, Sensors and Actuators B, May 1993, Vol. 13, 416.CrossRefGoogle Scholar
  10. 9.
    C. G. Claessens, U. Hahn, T. Torres, The Chemical Record, 2008, 8, 75.CrossRefGoogle Scholar
  11. 10.
    Gema de la Torre, P. Vσzquez, F. Agully-Lypez, T. Torres, Chem. Rev., 2004, 104, 3723.CrossRefGoogle Scholar
  12. 11.
    M. O. Senge, M. Fazekas, E. G. A. Notaras, W. J. Blau, M. Zawadzka, O. B. Locos, E. M. Ni, Mhuircheartaigh Adv. Mater., 2007, 19, 2737.CrossRefGoogle Scholar
  13. 12.
    S. Venugopal Rao, N. Venkatram, L. Giribabu, D. Narayana Rao, J. Appl. Phys., 2009, 053109, 105.Google Scholar
  14. 13.
    D. Dini, G. Ying Yang, M. Hanack, J. Chem. Phys., 2003, 4857, 119.Google Scholar
  15. 14.
    C. Colomban, E. V. Kudrik, P. Afanasiev, A. B. Sorokin, J. Am. Chem. Soc., 2014, 136, 11321.CrossRefGoogle Scholar
  16. 15.
    Y. Zorlu, F. Dumoulin, D. Bouchu, V. Ahsen, D. Lafont, Tetrahedron Lett., 2010, 51, 6615.CrossRefGoogle Scholar
  17. 16.
    J.-P. Taquet, C. Frochot, V. Manneville, M. Barberi-Heyob, Curr. Med. Chem., 2007, 14, 1673.CrossRefGoogle Scholar
  18. 17.
    X.-F. Zhang, Y. Lin, W. Guo, J. Zhu, Spectrochim. Acta. Part A: Mol. Biomol. Spectros., 2014, 133, 752.CrossRefGoogle Scholar
  19. 18.
    C. Göl, M. Malkoç, S. Ye ilot, M. Durmu, Dyes and Pigments, 2014, 111, 81.CrossRefGoogle Scholar
  20. 19.
    R. Heukers, P. M. P. van Bergen en Henegouwen, S. Oliveira, Nanomedicine: Nanotechnology, Biology, and Medicine, 2014, 10, 1441.Google Scholar
  21. 20.
    Z. Chen, P. Xu, J. Chen, H. Chen, P. Hu, X. Chen, L. Lin, Y. Huang, K. Zheng, S. Zhou, R. Li, S. Chen, J. Liu, J. Xue, M. Huang, Acta Biomaterialia, 2014, 10, 4257.CrossRefGoogle Scholar
  22. 21.
    L. M. O. Lourenço, P. M. R. Pereira, E. Maciel, M. Va´lega, F. M. J. Domingues, M. R. M. Domingues, M. G. P.M. S. Neves, J. A. S. Cavaleiro, R. Fernandes, J. P. C. Tome´, Chem. Commun., 2014, 50, 8363.CrossRefGoogle Scholar
  23. 22.
    J. D. Huang, P. C. Lo, Y. M. Chen, J. C. Lai, W. P. Fong, D. K. P. Ng, J. Inorg. Biochem., 2006, 100, 946.CrossRefGoogle Scholar
  24. 23.
    D. Lafonta, Y. Zorlub, H. Savoiec, F. Albrieuxd, V. Ahsenb, R. W. Boylec, F. Dumoulin, Photodiagnosis and Photodynamic Therapy, 2013, 10, 252.CrossRefGoogle Scholar
  25. 24.
    W. M. Sharman, J. E. van Lier, in The Porphyrin Handbook, Eds E. Kadish, K. M. Smith, R. Guiliard, Acad. Press, New York, 2003, Vol. 15, 1.CrossRefGoogle Scholar
  26. 25.
    V. N. Nemykin, E. A. Luk´yanets, ARKIVOC, 2010, Part I, 136.Google Scholar
  27. 26.
    M. K. Islyaikin, S. P. Konovalov, A. V. Lyubimtsev, R. P. Smirnov, A. Baran´ski, Izv. vuzov. Khimiya i khim. tekhnologiya [Higher Ed. Inst. Bull. Chemistry and Chem. Technol.], 1996, 39, No. 4—5, 28 (in Russian).Google Scholar
  28. 27.
    F. Baumann, B. Binert, G. Rosch, H. Vollmann, W. Wolf, Angew. Chem., 1956, 68, 133.CrossRefGoogle Scholar
  29. 28.
    V. F. Borodkin, Russ. Zh. Prikl. Khim., 1958, 31, 813 [J. Appl. Chem. (Engl. Transl.), 1958, 31].Google Scholar
  30. 29.
    S. A. Siling, S. V. Vinogradova, V. V. Korshak, V. N. Solov´ev, Dep. v VINITI [Dep. in VINITI] 1983, 16 pp. (in Russian).Google Scholar
  31. 30.
    M. K. Islyaikin, A. V. Lyubimtsev, R. P. Smirnov, A. Baran´ski, Izv. vuzov. Khimiya i khim. tekhnologiya [Higher Ed. Inst. Bull. Chemistry and Chem. Technol.], 1995, 38, No. 4—5, 81 (in Russian).Google Scholar
  32. 31.
    A. Lyubimtsev, A. Baranski, Russ. J. Org. Chem. (Engl. Transl.), 1998, 34, 1471 [Zh. Org. Khim., 1998, 34, 1531].Google Scholar
  33. 32.
    A. Sastre, T. Torres, M. Hanack, J. Org. Chem., 1990, 55, 2155.CrossRefGoogle Scholar
  34. 33.
    A. V. Lyubimtsev, Dr. Sci. Thesis (Chem.), FGBOU VPO IGKhTU, Ivanovo, 2013, 280 pp. (in Russian).Google Scholar
  35. 34.
    A. Baranski, A. Lyubimtsev, Russ. J. Org. Chem. (Engl. Transl.), 1998, 34, 1477 [Zh. Org. Khim., 1998, 34, 1542].Google Scholar
  36. 35.
    A. Baranski, A. Lyubimtsev, Russ. J. Org. Chem. (Engl. Transl.), 2000, 36, 725 [Zh. Org. Khim., 2000, 36, 752].Google Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • A. V. Lyubimtsev
    • 1
    • 2
  • N. V. Zheglova
    • 1
  • E. N. Smirnova
    • 1
  • S. A. Syrbu
    • 1
    • 2
  1. 1.Ivanovo State University of Chemistry and TechnologyIvanovoRussian Federation
  2. 2.Research Institute of Macroheterocyclic CompoundsIvanovoRussian Federation

Personalised recommendations