Skip to main content
SpringerLink
Log in

Reactions of metal promoted C-C-coupling of coordinated 1,10-phenanthrolines in the synthesis of electron-rich d-element 1,10-phenanthrocyanines

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The methods of C-C bond formation between free or coordinated 1,10-phenanthrolines are examined, and a new structural class of cyanine tetraazachromophores, the electron-rich d-element 1,10-phenanthrocyanines is presented, the role of metal promoted Csp2H-Csp2H coupling reactions in the synthesis of new metal 1,10-phenanthrocyanines is discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Sammes, P.G. and Yahioglu G., Chem. Soc. Rev., 1994, vol. 23, no. 5, pp. 327–334.

    Article  CAS  Google Scholar 

  2. Luman, C.R. and Castellano, F.N., in Comprehensive Coordination Chemistry. II: From Biology to Nanotechnology, Lever, A.B.O., Ed., Elsevier, 2003, vol. 1, pp. 25–39.

  3. Tzalis, D., Tor, Y., Failla, S., and Siegel, J.S., Tetrahedron Lett., 1995, vol. 36, no. 20, pp. 3489–3490.

    Article  CAS  Google Scholar 

  4. Demidov, V.N., Kukushkin, Yu.N., and Vedeneeva, L.N., Zh. Obshch. Khim., 1988, vol. 58, no. 4, pp. 741–746.

    CAS  Google Scholar 

  5. Zhidkova, O.B., Iretskii, A.V., and Demidov, V.N., Zh. Neorg. Khim., 1990, vol. 35, no. 5, pp. 1190–1195.

    CAS  Google Scholar 

  6. Ogawa Sh., J. Chem. Soc., Perkin Trans, I., 1977, no. 2, pp. 214–216.

  7. El’man, A.R. and Korneeva G.A., Ros. Khim. Zh. (Zh. Ros. Khim. Ob-va im., D.I. Mendeleeva), 2006, vol. 50, no. 4, pp. 115–127.

    Google Scholar 

  8. Stolyarov, I.P., Gaugash, Yu.V., Kryukova G.N., Kochubei, D.I., Vargaftik, M.N., and Moiseev, I.I., Izv. Akad. Nauk, Ser. Khim., 2004, no. 6, pp. 1147–1152.

  9. Stromnova, T.A., Platinum Metals Rev., 2003, vol. 47, no. 1, pp. 20–27.

    CAS  Google Scholar 

  10. Beer, R.H., Jimenez, J., and Drago, R.S., J. Org. Chem., 1993, vol. 58, no. 7, pp. 1746–1747.

    Article  CAS  Google Scholar 

  11. Yanagida, M., Singh, L., P., Sayama, K., Hara, K., Katoh, R., Islam, A., Sugihara, H., Arakawa, H., Nazeeruddin, M.K., and Grätzel, M., J. Chem. Soc., Dalton Trans., 2000, pp. 2817–2822.

  12. O’Neill, M.A. and Barton, J.K., Top. Curr. Chem., 2004, vol. 236, pp. 67–115.

    Google Scholar 

  13. RF Patent no. 2089555, publ. 10.09.1997, Byul. Izobret., 1997, no. 25.

  14. Borisov, A.N., Timonov, A.M., Timofeev, V.A., and Shagisultanova G.A., Zh. Neorg. Khim., 1996, vol. 41, no. 3, pp. 453–458.

    CAS  Google Scholar 

  15. Zheng Qingdong, He Guang, S., and Prasad Paras, N., J. Mater. Chem., 2005, vol. 15, pp. 579–587.

    Article  CAS  Google Scholar 

  16. Prostota, Ya.O., Cand. Sci. (Chem.) Dissertation, Kiev, 2002.

  17. Riesgo, E.C., Hu, Y.-Z., and Thummel, R.P., Inorg. Chem., 2003, vol. 42, no. 21, pp. 6648–6654.

    Article  CAS  Google Scholar 

  18. Saitoh Yutaka and Yamamoto Takakazu, Chem. Lett., 1995, vol. 9, no. 5, pp. 785–786.

    Google Scholar 

  19. Yan-He Guo, Hua-Kuan Lin, Qing-Chun Ge, Shou-Rong Zhu, J. Coord. Chem., 2004, vol. 57, no. 1, pp. 61–73.

    Article  CAS  Google Scholar 

  20. Heuft, M.A. and Fallis, A.G., Angew. Chem, Int. Ed., 2002, vol. 41, no. 23, pp. 4520–4523.

    Article  CAS  Google Scholar 

  21. Afanas’ev, V.V., Bespalova, N.B., and Beletskaya, I.P., Ros. Khim. Zh. (Zh. Ros. Khim. Ob-va im., D.I. Mendeleeva), 2006, vol. 50, no. 4, pp. 81–93.

    Google Scholar 

  22. Kang, S.-K., Lee, H.-W., Jang, S.-B., and Ho, P.-S., J. Org. Chem., 1996, vol. 61, no. 14, pp. 4720–4724.

    Article  CAS  Google Scholar 

  23. Bumagin, N.A., Sukhomlinova, L.I., Tolstaya, T.P., and Beletskaya, I.P., Zh. Org. Khim., 1996, vol. 32, no. 11, pp. 1724–1728.

    CAS  Google Scholar 

  24. Dalko, P.I., Tetrahedron, 1995, vol. 51, no. 28, pp. 7579–7653.

    Article  CAS  Google Scholar 

  25. Diaba, F., Lewis, I., Grignon-Dubois, M., and Navarre, S., J. Org. Chem., 1996, vol. 61, no. 14, pp. 4830–4832.

    Article  CAS  Google Scholar 

  26. Pozharskii, A.F., Teoreticheskie osnovy khimii geterotsiklov (Theoretical Fundamentals of the Chemistry of Heterocycles), Moscow: Khimiya, 1985.

    Google Scholar 

  27. Lay, P.A., Inorg. Chem., 1984, vol. 23, no. 26, pp. 4775–4777.

    Article  CAS  Google Scholar 

  28. Kozitsyna, N.Yu. and Moiseev, I.I., Usp. Khim., 1995, vol. 64, no. 1, pp. 51–65.

    CAS  Google Scholar 

  29. Kaim, W., Coord. Chem. Rev., 1987, vol. 76, pp. 187–235.

    Article  CAS  Google Scholar 

  30. Constable, E.C., Inorg. Chim. Acta, 1984, vol. 82, no. 1, pp. 53–57.

    Article  CAS  Google Scholar 

  31. Kunkely, H. and Vogler, A., J. Amer. Chem. Soc., 1990, vol. 112, no. 4, pp. 5625–5630.

    Article  CAS  Google Scholar 

  32. Rakhimov, R.D., Vainshtein, Yu.A., Lileeva, E.V., Zheligovskaya, N.N., Mel’nikov, M.Ya., and Butin, K.P., Izv. Akad. Nauk, Ser. Khim., 2003, no. 5, pp. 1089–1095.

  33. Kato, M. and Takahashi, J., Acta Crystallogr., Sect., C, 1999, vol. C55, pp. 1809–1812.

    Article  CAS  Google Scholar 

  34. Demidov, V.N., Savinova, A.I., Zinchenko, A.V., and Simanova, S.A., Abstracts of Papers, XXIII Int. Chugaev Conf. on Coordination Chemistry, September 4–7, 2007, Odessa, IONKh im., N.S. Kurnakova Ross. Akad. Nauk, pp. 389–390.

  35. Case, F.H., J. Heterocycl. Chem., 1964, vol. 1, no. 1, p. 112.

    Article  Google Scholar 

  36. Summers, L.A., Adv. Heterocycl. Chem., 1978, vol. 22, no. 1, pp. 1–69.

    Article  CAS  Google Scholar 

  37. Rice, C.R. and Anderson, K.M., Polyhedron, 2000, vol. 19, no. 4, pp. 495–498.

    Article  CAS  Google Scholar 

  38. Hu, Y.-Z., Xiang Qin, and Thummel, R.P., Inorg. Chem., 2002, vol. 41, no. 13, pp. 3423–3428.

    Article  CAS  Google Scholar 

  39. Griffiths, P.M., Loiseau, F., Puntoriero, F., Serroni, S., and Campagna, S., Chem. Commun., 2000, no. 12, pp. 2297–2298.

  40. Toyota, S., Woods, C.R., Benaglia, M., Hardcastle, K., and Siegel, J.S., Angew. Chem. Int. Ed., 2001, vol. 40, pp. 751–754.

    Article  CAS  Google Scholar 

  41. Cookson, P.G. and Deacon G.B., Austral. J. Chem., 1972, vol. 25, no. 10, pp. 2095–2105.

    CAS  Google Scholar 

  42. Kitagawa Mako, Iwaku Masahiro, and Oyama Noboru, Polym. Adv. Technol., 1995, vol. 6, no. 3, pp. 204–212.

    Article  Google Scholar 

  43. Borisov, A.N., Timonov, A.M., and Shagisultanova G.A., Zh. Prikl. Khim., 1994, vol. 67, no. 10, pp. 1604–1607.

    CAS  Google Scholar 

  44. Borisov, A.N., Timonov, A.M., and Shagisultanova G.A., Zh. Prikl. Khim., 1995, vol. 68, no. 2, pp. 333–334.

    CAS  Google Scholar 

  45. Xiao Dongrong, Hou Yu, Wang Enbo, Lü Jian, Li Yangguang, Xu Lin, and Hu Changwen, Inorg. Chem. Commun., 2004, vol. 7, no. 3, pp. 437–439.

    Article  Google Scholar 

  46. Liu Cai-Ming, Gao Song, and Kou Hui-Zhong, Chem. Commun., 2001, no. 10, pp. 1670–1671.

  47. Kobayashi Nagao, in: The Porphyrin Handbook, vol. 15: Phthalocyanines: Synthesis, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., Amsterdam: Academic Press, 1999, pp. 161–262.

    Google Scholar 

  48. Demidov, V.N., Kukushkin, Yu.N., Iretskii, A.V., Zhidkova, O.B., and Vedeneeva, L.N., Zh. Obshch. Khim., 1989, vol. 59, no. 8, pp. 1886–1887.

    CAS  Google Scholar 

  49. Demidov, V.N., Denisov, I.A., Belyaev, A.N., Yakovlev, V.N., and Kukushkin, Yu.N., Koord. Khim., 1991, vol. 17, no. 12, pp. 1717–1718.

    CAS  Google Scholar 

  50. Demidov, V.N., Zh. Prikl. Khim., 1992, vol. 65, no. 7, pp. 1654–1658.

    CAS  Google Scholar 

  51. Demidov, V.N., Zh. Prikl. Khim., 1993, vol. 66, no. 12, pp. 2822–2824.

    CAS  Google Scholar 

  52. Vedeneeva, L.N. and Demidov, V.N., Abstracts of Papers, Int. Conference “Communication ways and scientific achievements of Evrasia people,” Perm’ State Technological Inst., 1997, Section IV, pp. 228–229.

  53. Vedeneeva, L.N. and Demidov, V.N., Collection of Scientific Papers of Perm’ State Technological Inst., Bekker, V.F., Ed., 1998, no. 1, p. 16.

  54. Demidov, V.N., Aleksandrova, E.A., and Vedeneeva, L.N., Abstracts of Papers, XX Int. Chugaev Conf. on Coord. Chemistry, June 25–29, 2001, Rostov-on-Don, pp. 30–31.

  55. Demidov, V.N., Aleksandrova, E.A., and Vedeneeva, L.N., Abstracts of Papers, XX Int. Chugaev Conf. on Coord. Chemistry, June 25–29, 2001, Rostov-on-Don, pp. 32–33.

  56. Demidov, V.N., Puzenko, V.G., Konovalov, L.V., and Libov, V.S., Abstracts of Papers, XXII Int. Chugaev Conf. on Coord. Chemistry, June 20–24, 2005, Kishinev, pp. 337–338.

  57. Demidov, V.N., Puzenko, V.G., and Potapov, P.Yu., Abstracts of Papers, XXII Int. Chugaev Conf. on Coord. Chemistry, June 20–24, 2005 Kishinev, pp. 338–339.

  58. Demidov, V.N., Puzenko, V.G., Savinova, A.I., Panina, N.S., Pakhomova, T.B., Vedeneeva, L.N., and Simanova, S.A., Vest. MITKhT, 2007, vol. 2, no. 3, pp. 36–43.

    Google Scholar 

  59. Demidov, V.N., Savinova, A.I., Pakhomova, T.B., and Zinchenko, A.V., Abstracts of Papers, XXIII Int. Chugaev Conf. on Coord. Chemistry, Sept. 4–7, 2005, Odessa, pp. 388–389.

  60. Demidov, V.N., Savinova, A.I., Pakhomova, T.B., and Alexandrova, E.A., Abstracts of Papers, XVI Int. Conf. on Chemical Thermodynamics in Russia (RCCT 2007), X Int. Conf. on the Problems of Solvation and Complex Formation in Solutions, Suzdal, July 1–6, 2007, vol. I, pp. 2/S–192.

  61. Panina, N.S., Demidov, V.N., and Simanova, S.A., Zh. Obshch. Khim., 2008, vol. 78, no. 5, pp. 771–776.

    Google Scholar 

  62. Panina, N.S., Demidov, V.N., and Simanova, S.A., Zh. Obshch. Khim., 2008, vol. 78, no. 5, pp. 777–782.

    Google Scholar 

  63. RF Inventor’s Sertificate no. 1467469, published March 23, 1989.

  64. RF Inventor’s Sertificate, no. 1485074, published June 7, 1989.

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Technological Institute (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    V. N. Demidov, S. A. Simanova, A. I. Savinov & T. B. Pakhomov

Authors
  1. V. N. Demidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Simanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. Savinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. B. Pakhomov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. N. Demidov.

Additional information

Original Russian Text © V.N. Demidov, S.A. Simanova, A.I. Savinov, T. B. Pakhomov, 2009, published in Rossiiskii Khimicheskii Zhurnal, 2010, Vol. 53, No. 1, pp. 128–133.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Demidov, V.N., Simanova, S.A., Savinov, A.I. et al. Reactions of metal promoted C-C-coupling of coordinated 1,10-phenanthrolines in the synthesis of electron-rich d-element 1,10-phenanthrocyanines. Russ J Gen Chem 79, 2807–2814 (2009). https://doi.org/10.1134/S1070363209120391

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363209120391

Keywords

Search

Navigation