Skip to main content
SpringerLink
Log in

meso-Aryltetrabenzoporphyrins. Synthesis and properties

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The most considerable achievements in the synthesis and investigations of meso-aryltetrabenzoporphyrins and their metal complexes are reviewed. The choice of the route to, and the properties of, these compounds depends on the nature and number of meso-aryl substituents. The reviewed synthetic methods are compared. Selected physicochemical and spectroscopic properties of meso-aryltetrabenzoporphyrins are analyzed.

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. M. R. Tarasevich, K. L. Radyushkina, Usp. Khim., 1980, 49, 1498 [Russ. Chem. Rev., 1980, 49 (Engl. Transl.)].

    CAS  Google Scholar 

  2. G. McLendon, D. C. Miller, J. Chem. Soc., Chem. Commun., 1980, 11, 533.

    Article  Google Scholar 

  3. Y. Umesawa, T. Yamamura, J. Electrochem. Soc., 1979, 126, 705.

    Article  Google Scholar 

  4. S. A. Lebedev, V. N. Kopranenkov, L. S. Goncharova, Zh. Tekh. Fiz. [Journal of Technical Physics], 1980, 51, 1749 (in Russian).

    Google Scholar 

  5. O. N. Korotaev, E. I. Donskoi, V. I. Glyadkovskii, V. N. Kopranenkov, Opt. Spektrosk. [Optics and Spectroscopy], 1984, 54, 145 (in Russian).

    Google Scholar 

  6. A. Lavi, F. M. Johnson, B. Ehrenberg, Chem. Phys. Lett., 1994, 231, 144.

    Article  CAS  Google Scholar 

  7. I. B. Rietveld, E. Kim, S. A. Vinogradov, Tetrahedron, 2003, 59, 3821.

    Article  CAS  Google Scholar 

  8. W. P. Ambrose, W. E. Moerner, Chem. Phys., 1990, 144, 71.

    Article  CAS  Google Scholar 

  9. N. Ono, S. Ito, C. H. Wu, C. H. Chen, T. C. Wen, Chem. Phys., 2000, 262, 467.

    Article  CAS  Google Scholar 

  10. R. P. Linstead, E. G. Noble, J. Am. Chem. Soc., 1937, Part II, 933.

  11. J. H. Helberger, A. Rubai, D. E. Helver, J. Liebigs Ann. Chem., 1938, 536, 197.

    Article  Google Scholar 

  12. J. H. Helberger, D. E. Helver, J. Liebigs Ann. Chem., 1938, 536, 173.

    Article  CAS  Google Scholar 

  13. V. N. Kopranenkov, S. N. Dashkevich, E. A. Luk’yanets, Zh. Obshch. Khim., 1981, 51, 2513 [J. Gen. Chem. USSR, 1981, 51 (Engl. Transl.)].

    CAS  Google Scholar 

  14. USSR Inventor’s Certificate 889 675; Byull. Izobret., 1981, 46 (in Russian).

  15. D. V. G. L. N. Rao, F. J. Aranda, D. E. Remy, J. F. Roach, J. Nonlinear Opt. Phys. Mater., 1994, 3, 511.

    Article  CAS  Google Scholar 

  16. M. Yasuike, T. Yamaoka, O. Ohno, M. Sakuragi, K. Ichimura, Inorg. Chim. Acta, 1991, 184, 191.

    Article  CAS  Google Scholar 

  17. E. Gross, B. Ehrenberg, F. M. Johnson, Photochem. Photobiol., 1993, 57, 808.

    Article  CAS  Google Scholar 

  18. M. Brunel, F. Chaput, S. A. Vinogradov, B. Campagne, M. Canva, J. P. Boilot, Chem. Phys., 1997, 218, 301.

    Article  CAS  Google Scholar 

  19. A. Lavi, F. M. Johnson, B. Ehrenberg, Chem. Phys. Lett., 1994, 231, 144.

    Article  CAS  Google Scholar 

  20. J. S. Friedberg, C. Skema, E. D. Baum, J. Burdick, S. A. Vinogradov, D. F. Wilson, A. D. Horan, I. Nachamkin, J. Antimicrob. Chemother., 2001, 48, 105.

    Article  CAS  Google Scholar 

  21. R. L. Lipson, E. J. Baldes, A. M. Olsen, J. Natl. Cancer Inst., 1961, 26, 1.

    CAS  Google Scholar 

  22. O. S. Finikova, S. E. Aleshchenkov, R. P. Brinas, A. V. Cheprakov, P. J. Carroll, S. A. Vinogradov, J. Org. Chem., 2005, 70, 4617.

    Article  CAS  Google Scholar 

  23. V. Kral, H. Furuta, K. Shreder, V. Lynch, J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595.

    Article  CAS  Google Scholar 

  24. N. Kobayashi, Bull. Chem. Soc. Jpn, 2002, 75, 1.

    Article  CAS  Google Scholar 

  25. Porfiriny: struktura, svoistva, sintez [Porphyrins: Structures, Properties, and Synthesis], Ed. N. S. Enikolopyan, Nauka, Moscow, 1987, 333 pp. (in Russian).

    Google Scholar 

  26. P. Rothemund, J. Am. Chem. Soc., 1939, 61, 2912.

    Article  CAS  Google Scholar 

  27. A. D. Adler, F. P. Longo, J. D. Finarelli, J. Goldmacher, J. Assour, L. Korsakoff, J. Org. Chem., 1967, 32, 467.

    Article  Google Scholar 

  28. E. A. Luk’yanets, S. N. Dashkevich, N. Kobayashi, Zh. Obshch. Khim., 1993, 63, 1411 [Russ. J. Gen. Chem., 1993, 63 (Engl. Transl.)].

    Google Scholar 

  29. G. Liu, T. Shi, X. Cao, X. Liu, Synth. React. Inorg. Met.-Org. Chem., 1994, 24, 1127.

    Article  CAS  Google Scholar 

  30. T. Shi, X. Zhang, W. Liu, B. Jia, G. Liu, Chem. J. Chin. Univ., 1998, 19, 1026.

    CAS  Google Scholar 

  31. V. N. Kopranenkov, E. A. Makarova, E. A. Luk’yanets, Khim. Geterotsikl. Soedin., 1988, 480 [Chem. Heterocycl. Compd., 1988 (Engl. Transl.)].

  32. N. E. Galanin, N. A. Kolesnikov, E. V. Kudrik, G. P. Shaposhnikov, Zh. Org. Khim., 2004, 40, 297 [Russ. J. Org. Chem., 2004, 40 (Engl. Transl.)].

    Google Scholar 

  33. N. E. Galanin, E. V. Kudrik, G. P. Shaposhnikov, Zh. Org. Khim., 2003, 39, 1254 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].

    Google Scholar 

  34. K. Ichimura, M. Sakuragi, H. Morii, M. Yasuike, M. Fukui, O. Ohno, Inorg. Chim. Acta, 1991, 182, 83.

    Article  CAS  Google Scholar 

  35. D. E. Remy, Tetrahedron Lett., 1983, 24, 1451.

    Article  CAS  Google Scholar 

  36. V. N. Kopranenkov, E. A. Makarova, S. N. Dashkevich, E. A. Luk’yanets, Khim. Geterotsikl. Soedin., 1982, 1563 [Chem. Heterocycl. Compd., 1982 (Engl. Transl.)].

  37. V. M. Rodionov, E. I. Chukhina, Zh. Obshch. Khim., 1944, 14, 325 [J. Gen. Chem. USSR, 1944, 14 (Engl. Transl.)].

    CAS  Google Scholar 

  38. N. E. Galanin, E. V. Kudrik, G. P. Shaposhnikov, Zh. Obshch. Khim., 1999, 69, 1542 [Russ. J. Gen. Chem., 1999, 69 (Engl. Transl.)].

    Google Scholar 

  39. N. E. Galanin, Ph.D. (Chem.) Thesis, IGKhTU, Ivanovo, 2002, 133 pp. (in Russian).

  40. RF Pat. 2 215 003; Byull. Izobret., 2003, 30 (in Russian).

  41. V. P. Kulinich, G. P. Shaposhnikov, V. E. Maizlish, in Teoreticheskie i prakticheskie aspekty krasheniya tekstil’nykh materialov i sinteza krasitelei [Theoretical and Practical Aspects of Textile Dyeing and Dye Synthesis], Ed. B. N. Mel’nikov, IKhTI, Ivanovo, 1991, 43 (in Russian).

    Google Scholar 

  42. N. E. Galanin, E. V. Kudrik, G. P. Shaposhnikov, Zh. Obshch. Khim., 1997, 67, 1393 [Russ. J. Gen. Chem., 1997, 67 (Engl. Transl.)].

    Google Scholar 

  43. N. E. Galanin, E. V. Kudrik, G. P. Shaposhnikov, Zh. Obshch. Khim., 1998, 68, 1740 [Russ. J. Gen. Chem., 1998, 68 (Engl. Transl.)].

    Google Scholar 

  44. I. B. Rietveld, E. Kim, S. A. Vinogradov, Tetrahedron, 2003, 59, 3821.

    Article  CAS  Google Scholar 

  45. S. A. Vinogradov, D. F. Vilson, Tetrahedron Lett., 1998, 39, 8935.

    Article  CAS  Google Scholar 

  46. O. Finikova, A. Cheprakov, I. Beletskaya, S. Vinogradov, Chem. Commun., 2001, 261.

  47. O. S. Finikova, A. V. Cheprakov, S. Yu. Chernov, M. A. Filatov, S. A. Vinogradov, I. P. Beletskaya, Dokl. Akad. Nauk, 2003, 391, 781 [Dokl. Chem., 2003 (Engl. Transl.)].

    Google Scholar 

  48. O. S. Finikova, A. V. Cheprakov, I. P. Beletskaya, P. J. Carroll, S. A. Vinogradov, J. Org. Chem., 2004, 69, 522.

    Article  CAS  Google Scholar 

  49. J. R. Platt, Radiat. Biol., 1956, 3, 71.

    CAS  Google Scholar 

  50. M. Gouterman, J. Chem. Phys., 1959, 30, 1139.

    Article  CAS  Google Scholar 

  51. K. N. Solov’ev, Opt. Spektrosk. [Optics and Spectroscopy], 1961, 10, 737 (in Russian).

    Google Scholar 

  52. N. E. Galanin, E. V. Kudrik, G. P. Shaposhnikov, Zh. Org. Khim., 2006, 42, 619 [Russ. J. Org. Chem., 2006, 42 (Engl. Transl.)].

    Google Scholar 

  53. Elektronnye spektry ftalotsianinov i rodstvennykh soedinenii. Katalog [Electronic Spectra of Phthalocyanines and Related Compounds. A Catalog], Ed. E. A. Luk’yanets, NIITEKhIM, Cherkassy, 1989, 94 pp. (in Russian).

    Google Scholar 

  54. G. P. Shaposhnikov, V. F. Borodkin, M. I. Fedorov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1981, 24, 1485 [Bull. High Schools, Chem. Chem. Technol., 1981, 24 (Engl. Transl.)].

    CAS  Google Scholar 

  55. V. P. Kulinich, S. I. Vasil’ev, G. P. Shaposhnikov, V. E. Maizlish, Koord. Khim., 1997, 23, 785 [Russ. J. Coord. Chem., 1997, 23 (Engl. Transl.)].

    Google Scholar 

  56. S. I. Vasil’ev, V. P. Kulinich, G. P. Shaposhnikov, R. P. Smirnov, Zh. Obshch. Khim., 1988, 68, 1325 [J. Gen. Chem. USSR, 1988, 68 (Engl. Transl.)].

    Google Scholar 

  57. A. J. Gordon, R. A. Ford, The Chemist’s Companion, Wiley, New York—London—Sydney—Toronto, 1972.

    Google Scholar 

  58. Analytikum. Methoden der analytischen Chemie und ihre theoretischen Grundlagen, VEB Deutscher Verlag für Grund-stoffindustrie, Leipzig, 1971.

  59. G. P. Shaposhnikov, V. P. Kulinich, V. E. Maizlish, Uspekhi khimii porfirinov [Achievements in the Chemistry of Porphyrins], Ed. O. A. Golubchikov, Izd. NII Khimii SPbGU, St. Petersburg, 1999, Vol. 2, 190 (in Russian).

    Google Scholar 

  60. R. Cheng, Y. Chen, S. Wang, C. Chuang, Polyhedron, 1993, 12, 1353.

    Article  CAS  Google Scholar 

  61. M. Lee, S. Liou, R. Cheng, J. Am. Soc. Mass Spectrom., 1997, 12, 62.

    Article  CAS  Google Scholar 

  62. G. P. Shaposhnikov, Yu. M. Osipov, V. P. Kulinich, R. P. Smirnov, Tezisy dokladov XVII Vsesoyuznogo Chugaevskogo soveshchaniya po khimii kompleksnykh soedinenii [Abstrs. XVII All-Union Chugaev Conf. on the Chemistry of Complexes], Minsk, 1990, Part 1, 41 (in Russian).

  63. G. P. Shaposhnikov, V. F. Borodkin, M. I. Fedorov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1978, 24, 1485 [Bull. High Schools, Chem. Chem. Technol., 1978, 24 (Engl. Transl.)].

    Google Scholar 

  64. V. E. Maizlish, G. P. Shaposhnikov, V. P. Kulinich, O. V. Shishkina, R. P. Smirnov, Zh. Obshch. Khim., 1997, 67, 846 [Russ. J. Gen. Chem., 1997, 67 (Engl. Transl.)].

    Google Scholar 

  65. K. Ichimura, M. Sakuragi, H. Morii, M. Yasuike, Y. Toba, M. Fukui, O. Ohno, Inorg. Chim. Acta, 1991, 186, 95.

    Article  CAS  Google Scholar 

  66. R. Cheng, Y. Chen, C. Chuang, Heterocycles, 1992, 34, 1.

    Article  Google Scholar 

  67. N. E. Galanin, E. V. Kudrik, G. P. Shaposhnikov, Zh. Obshch. Khim., 2000, 70, 1379 [Russ. J. Gen. Chem., 2000, 70 (Engl. Transl.)].

    Google Scholar 

  68. E. V. Kudrik, M. K. Islyaikin, S. V. Frantseva, Zh. Obshch. Khim., 1997, 67, 1202 [Russ. J. Gen. Chem., 1997, 67 (Engl. Transl.)].

    Google Scholar 

  69. N. E. Galanin, E. V. Kudrik, G. P. Shaposhnikov, Zh. Obshch. Khim., 2002, 72, 1198 [Russ. J. Gen. Chem., 2002, 72 (Engl. Transl.)].

    Google Scholar 

  70. N. E. Galanin, E. V. Kudrik, M. E. Lebedev, V. V. Aleksandriiskii, G. P. Shaposhnikov, Zh. Org. Khim., 2005, 42, 306 [Russ. J. Org. Chem., 2005, 42 (Engl. Transl.)].

    Google Scholar 

  71. N. E. Galanin, E. V. Kudrik, G. P. Shaposhnikov, Zh. Org. Khim., 2001, 35, 725 [Russ. J. Org. Chem., 2001, 35 (Engl. Transl.)].

    Google Scholar 

  72. M. O. Senge, I. Bischoff, Tetrahedron Lett., 2004, 45, 1647.

    Article  CAS  Google Scholar 

  73. M. J. S. Dewar, E. G. Zoebibisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.

    Article  CAS  Google Scholar 

  74. K. N. Solov’ev, V. A. Mashenkova, A. T. Gradyushko, A. E. Turkova, Zh. Prikl. Spektrosk., 1970, 13, 339 [J. Appl. Spectr., 1970, 13 (Engl. Transl.)].

    Google Scholar 

  75. D. B. Berezin, O. V. Shukhto, N. E. Galanin, Koord. Khim., 2003, 29, 574 [Russ. J. Coord. Chem., 2003, 29 (Engl. Transl.)].

    Google Scholar 

  76. B. D. Berezin, T. I. Potapova, E. B. Karavaeva, Zh. Fiz. Khim., 1978, 52, 2198 [Russ. J. Phys. Chem., 1978, 52 (Engl. Transl.)].

    CAS  Google Scholar 

  77. D. B. Berezin, B. D. Berezin, Uspekhi khimii porfirinov [Achievements in the Chemistry of Porphyrins], Ed. O. A. Golubchikov, Izd. NII Khimii SPbGU, St. Petersburg, 1999, Vol. 2, 128 (in Russian).

    Google Scholar 

  78. M. O. Senge, in Porphyrin Handbook, Eds K. Smith, K. Kadish, and R. Guilard, Wiley, San Diego, 1999, Vol. 1, 239.

    Google Scholar 

  79. M. O. Senge, G. J. Medforth, T. P. Forsyth, Inorg. Chem., 1997, 36, 1149.

    Article  CAS  Google Scholar 

  80. B. D. Berezin, Koordinatsionnye soedineniya porfirinov i ftalotsianina [Coordination Compounds of Porphyrins and Phthalocyanine], Nauka, Moscow, 1978, 278 pp. (in Russian).

    Google Scholar 

  81. D. B. Berezin, O. V. Toldina, E. V. Kudrik, Zh. Obshch. Khim., 2003, 73, 1383 [Russ. J. Gen. Chem., 2003, 73 (Engl. Transl.)].

    Google Scholar 

  82. D. B. Berezin, I. Yu. Bazlova, O. V. Malkova, V. G. Andrianov, Koord. Khim., 2000, 26, 315 [Russ. J. Coord. Chem., 2000, 26 (Engl. Transl.)].

    Google Scholar 

  83. N. S. Dudkina, P. A. Shatunov, E. M. Kuvshinova, A. S. Semeikin, O. A. Golubchikov, Zh. Obshch. Khim., 1998, 68, 2042 [Russ. J. Gen. Chem., 1998, 68 (Engl. Transl.)].

    Google Scholar 

  84. M. I. Bazanov, R. P. Smirnov, M. A. Zharnikova, Tezisy dokladov II Mezhdunarodnogo seminara “Elektrokhimiya v praktike i teorii” [Abstrs. II Int. Seminar “Electrochemistry in Practice and Theory”], Lódź, 1994, 62 (in Russian).

  85. M. I. Bazanov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1988, 31, 62 [Bull. High Schools, Chem. Chem. Technol., 1988, 31 (Engl. Transl.)].

    CAS  Google Scholar 

  86. M. I. Bazanov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1992, 35, 40 [Bull. High Schools, Chem. Chem. Technol., 1992, 35 (Engl. Transl.)].

    CAS  Google Scholar 

  87. A. A. Evseev, M. I. Bazanov, N. E. Galanin, A. V. Petrov, G. Andrijewski, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 2004, 47, 24 [Bull. High Schools, Chem. Chem. Technol., 2004, 47 (Engl. Transl.)].

    Google Scholar 

  88. M. I. Bazanov, M. A. Zharnikova, O. E. Ulitina, I. A. Kapranova, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1993, 36, 64 [Bull. High Schools, Chem. Chem. Technol., 1993, 36 (Engl. Transl.)].

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ivanovo State University of Chemical Technology, 7 prosp. F. Engel’sa, 153460, Ivanovo, Russian Federation

    N. E. Galanin, E. V. Kudrik & G. P. Shaposhnikov

Authors
  1. N. E. Galanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Kudrik
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. P. Shaposhnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. E. Galanin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1565–1580, August, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Galanin, N.E., Kudrik, E.V. & Shaposhnikov, G.P. meso-Aryltetrabenzoporphyrins. Synthesis and properties. Russ Chem Bull 57, 1595–1610 (2008). https://doi.org/10.1007/s11172-008-0207-4

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-008-0207-4

Key words

Search

Navigation