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Synthesis of meso-phenyl-substituted porphyrins as starting compounds for the preparation of porphyrin-containing polymers

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Russian Chemical Bulletin Aims and scope

Abstract

Data on the synthesis of symmetrical and unsymmetrical meso-phenyl-substituted porphyrins, which are building blocks for porphyrin-based polymers of different structure, are analyzed. Methods for the porphyrin ring construction and modification by active functional groups for further immobilization onto a polymer or preparation of porphyrin monomers are considered.

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References

  1. L. R. Milgrom, The Colours of Life, Oxford University Press, Oxford, 1997.

    Google Scholar 

  2. F.-P. Montforts, B. Gerlach, and F. Hoper, Chem. Rev., 1994, 94, 327.

    Article  CAS  Google Scholar 

  3. V. Ya. Bykhovskii, in Uspekhi khimii porfirinov [Advances in Porphyrin Chemistry], Ed. O. A. Golubchikov, Izd-vo NII Khim. SPbGU, S.-Peterburg, 1997, vol. 1, 27 (in Russian).

    Google Scholar 

  4. G. Britton, The Biochemistry of Natural Pigments, Cambridge University Press, Cambridge, 1983.

    Google Scholar 

  5. Khimiya biologicheski aktivnykh prirodnykh soedinenii [The Chemistry of Biologically Active Natural Compounds], Ed. N. A. Preobrazhensky, R. P. Evstigneeva, Khimiya, Moscow, 1976, 512 pp. (in Russian).

    Google Scholar 

  6. O. V. Serebrennikova, Evolyutsiya tetrapirrol’nykh pigmentov v osadochnykh otlozheniyakh [Evolution of Tetrapyrrole Pigments in Sedimentary Deposits] Nauka, Novosibirsk, 1988, 140 pp. (in Russian).

    Google Scholar 

  7. O. V. Serebrennikova and T. V. Belokon’, Geokhimiya porfirinov [Geochemistry of Porphyrins], Nauka, Novosibirsk, 1984, 88 pp. (in Russian).

    Google Scholar 

  8. D. Wtshrle, J. Porphyrins Phthalocyanines, 2000, 4, No. 4, 418.

    Article  Google Scholar 

  9. Porfiriny: struktura, svoistva, sintez [Porphyrins: Structure, Properties, and Synthesis], Ed. N. S. Enikolopyan, Nauka, Moscow, 1985, 333 pp. (in Russian).

    Google Scholar 

  10. A. S. Semeikin and O. I. Koifman, Sovremennyi organicheskii sintez [Modern Organic Synthesis], Khimiya, Moscow, 2003, 361 (in Russian).

    Google Scholar 

  11. P. Rothemund, J. Am. Chem. Soc., 1935, 57, 2010.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. P. Rothemund, J. Am. Chem. Soc., 1941, 63, 267.

    Article  CAS  Google Scholar 

  14. R. H. Ball, G. D. Dorough, and M. A. Calvin, J. Am. Chem. Soc., 1946, 68, 2278.

    Article  CAS  Google Scholar 

  15. J. H. Priesthoff and C. V. Banks, J. Am. Chem. Soc., 1954, 76, 937.

    Article  CAS  Google Scholar 

  16. M. M. Williamson, C. M. Prosser-McCartha, S. Mukundan, Jr., and C. L. Hill, Inorg. Chem., 1988, 27, 1061.

    Article  CAS  Google Scholar 

  17. O. Bortolini, M. Ricci, B. Mennier, P. Frant, I. Ascone, and J. Goulon, Nouv. J. Chem., 1986, 10, 39.

    CAS  Google Scholar 

  18. U.S. Pat. 3.076.813, 1963.

  19. A. Petit, A. Loupy, P. Mallard, and M. Momenteau, Synth. Commun., 1992, 22, 1137.

    Article  CAS  Google Scholar 

  20. P. Laszlo and J. Luchetti, Chem. Lett., 1993, 449.

  21. M. Onaka, T. Shinoda, Y. Izimi, and E. Nolon, Chem. Lett., 1993, 117.

  22. C. M. Drain and X. Gong, Chem. Commun., 1997, 2117.

  23. G. A. Mirafzal, H. M. Bosse, and J. M. Summer, Tetrahedron Lett., 1999, 40, 623.

    Article  CAS  Google Scholar 

  24. D. V. Thomas and A. E. Martell, J. Am. Chem. Soc., 1956, 78, 1335.

    Article  Google Scholar 

  25. A. D. Adler, E. R. Longo, and W. Shergalis, J. Am. Chem. Soc., 1964, 86, 3145.

    Article  CAS  Google Scholar 

  26. A. Treibs and H. Haberle, J. Liebigs Ann. Chem., 1968, 718, 183.

    Article  CAS  Google Scholar 

  27. D. Dolphin, J. Heterocycl. Chem., 1970, No. 2, 275.

  28. A. D. Adler, F. R. Longo, J. D. Finarelli, J. Goldmacher, J. Assour, and L. Korsakoff, J. Org. Chem., 1967, 32, 476.

    Article  CAS  Google Scholar 

  29. J. B. Kim, J. J. Leonard, and F. R. Longo, J. Am. Chem. Soc., 1972, 94, 3986.

    Article  CAS  Google Scholar 

  30. M. J. Crossley, P. Thordarson, J. P. Bannerman, and P. J. Maynard, J. Porphyrins Phthalocyanines, 1998, 2, 511.

    Article  CAS  Google Scholar 

  31. A. S. Semeikin, O. I. Koifman, and B. D. Berezin, Khimiya Geterotsikl. Soedinenii, 1986, 798 [Chem. Heterocycl. Compd., 1986, No. 6 (Engl. Transl.)].

  32. N. E. Kagan, D. Mauzerall, and R. B. Merrifield, J. Am. Chem. Soc., 1977, 99, 5484.

    Article  CAS  Google Scholar 

  33. S. Banfi, F. Montanari, M. Penso, V. Sosnovskikh, and P. Vigano, Gazz. Chim. Ital., 1987, 117, 689.

    CAS  Google Scholar 

  34. A. S. Semeikin, N. G. Kuz’min, and O. I. Koifman, Zh. Prikl. Khim., 1988, 1426 [J. Appl. Chem. USSR, 1988, No. 6 (Engl. Transl.)].

  35. C.-C. Guo, X.-T. He, and G.-Y. Zhon, Chin. Org. Chem., 1991, 11, No. 4, 416.

    CAS  Google Scholar 

  36. S. M. S. Chauhan, B. B. Sahoo, and K. A. Srinivas, Synth. Commun., 2001, 31, No. 1, 33.

    Article  CAS  Google Scholar 

  37. A. M. Rocha Gonsalves, J. M. T. B. Varejao, and M. M. Pereira, J. Heterocycl. Chem., 1991, 28, No. 3, 635.

    Google Scholar 

  38. V. Sol, J. C. Blais, G. Bolbach, V. Carre, R. Granet, M. Guilloton, M. Spinro, and P. Krausz, Tetrahedron Lett., 1997, 38, 6391.

    Article  CAS  Google Scholar 

  39. K. Ohta, M. Ando, and I. Yamamoto, J. Porphyrins Phthalocyanines, 1999, 3, No. 4, 249.

    Article  CAS  Google Scholar 

  40. G. H. Barnett, M. F. Hudson, and K. M. Smith, J. Chem. Soc., Perkin Trans. 1, 1975, No. 14, 1401.

  41. G. H. Barnett, M. F. Hudson, and K. M. Smith, Tetrahedron Lett., 1973, 2887.

  42. K. Rousseau and D. Dolphin, Tetrahedron Lett., 1974, 4251.

  43. M. F. Zipplies, W. A. Lee, and T. C. Bruice, J. Am. Chem. Soc., 1986, 108, 4433.

    Article  CAS  Google Scholar 

  44. R. A. W. Johnstone, M. L. P. G. Nunes, M. M. Pereira, A. M. Rocha Gonsalves, and A. C. Serra, Heterocycles, 1996, 43, 1423.

    CAS  Google Scholar 

  45. J. S. Lindsey, I. C. Scheriman, H. C. Hsu, P. C. Kearney, and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827.

    Article  CAS  Google Scholar 

  46. J. S. Lindsey, H. C. Hsu, and I. C. Schreiman, Tetrahedron Lett., 1986, 27, 4969.

    Article  CAS  Google Scholar 

  47. A. M. d’A. Rocha Gonsalves, M. M. Pereira, A. C. Serra, R. A. W. Johnstone, and M. L. P. Nunes, J. Chem. Soc., Perkin Trans. 1, 1994, 2053.

  48. J. S. Lindsey, K. A. MacCrum, J. S. Tyhonas, and Y.-Y. Chuang, J. Org. Chem., 1994, 59, 579.

    Article  CAS  Google Scholar 

  49. F. Li, K. Yang, J. S. Tyhonas, K. A. MacCrum, and J. S. Lindsey, Tetrahedron, 1997, 53, 12339.

    Google Scholar 

  50. B. J. Littler, Y. Ciringh, and J. S. Lindsey, J. Org. Chem., 1999, 64, 2864.

    Article  CAS  Google Scholar 

  51. J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828.

    Article  CAS  Google Scholar 

  52. R. W. Wagner, D. C. Lawrence, and J. S. Lindsey, Tetrahedron Lett., 1987, 28, 3069.

    Article  CAS  Google Scholar 

  53. R. W. Wagner, F. Li, H. Du, and J. S. Lindsey, Org. Proc. Res. Dev., 1999, 3, 28.

    Article  CAS  Google Scholar 

  54. M. K. Safo, G. P. Gupta, F. A. Walker, and W. R. Scheidt, J. Am. Chem. Soc., 1991, 113, 5497.

    Article  CAS  Google Scholar 

  55. A. W. Van der Made, E. J. H. Hoppenbrauwer, R. J. M. Nolte, and W. Drenth, Rec. Trav. Chim. Pays-Bas., 1988, 107, 15.

    Google Scholar 

  56. M. Kihn-Botulinski and B. Meuier, Inorg. Chem., 1988, 27, 209.

    Article  CAS  Google Scholar 

  57. M. S. Chorghade, D. Dolphin, D. Dupre, D. R. Hill, E. G. Lee, and T. P. Wijesekera, Synthesis, 1996, 1320.

  58. S. Banfi, F. Montanari, and S. Quici, J. Org. Chem., 1987, 53, 2863.

    Article  Google Scholar 

  59. A. M. Rocha Gonsalves and M. M. Pereira, J. Heterocycl. Chem., 1985, 22, 931.

    Google Scholar 

  60. S. V. Vodzinskii, Ph.D. Thesis (chem.), Odessa State Univ., Odessa, 1990, 21 pp. (in Russian).

  61. M. Onaka, T. Shinoda, Y. Izumi, and E. Nolon, Tetrahedron Lett., 1993, 34, 2625.

    Article  CAS  Google Scholar 

  62. T. Shinoda, Y. Izumi, and M. Onaka, J. Chem. Soc., Chem. Commun., 1995, 1801.

  63. T. Shinoda, M. Onaka, and Y. Izumi, Chem. Lett., 1995, 493.

  64. J. S. Lindsey, in Metalloporphyrin-Catalayzed Oxidations, Eds F. Montanari and L. Casella, Kluwer Academic Publishers, Amsterdam, 1994, 49.

    Google Scholar 

  65. R. P. Bonar-Law, J. Org. Chem., 1996, 61, 3623.

    Article  CAS  Google Scholar 

  66. J. A. Anton and P. A. Loach, J. Heterocycl. Chem., 1975, 12, 573.

    CAS  Google Scholar 

  67. R. G. Little, J. A. Anton, P. A. Loach, and J. A. Ibers, J. Heterocycl. Chem., 1975, 12, 343.

    CAS  Google Scholar 

  68. J. S. Lindsey, S. Prathapan, T. E. Johnson, and R. W. Wagner, Tetrahedron, 1994, 50, 8941.

    Article  CAS  Google Scholar 

  69. S. Noblat, O. Dietrich-Buchecker, and J.-P. Sauvage, Tetrahedron Lett., 1987, 28, 5829.

    Article  CAS  Google Scholar 

  70. I. Tabushi, K.-I. Sakai, and K. Yamamura, Tetrahedron Lett., 1978, 19, 1821.

    Article  Google Scholar 

  71. I. Tabushi, S.-I. Kugimiga, M. G. Kinnard, and T. Sasaki, J. Am. Chem. Soc., 1985, 107, 4192.

    Article  CAS  Google Scholar 

  72. J. P. Collman, D. A. Tyvoll, L. L. Ching, and H. T. Fish, J. Org. Chem., 1995, 60, 1926.

    Article  CAS  Google Scholar 

  73. J. P. Collman, H. T. Fish, P. S. Wagenknecht, D. A. Tyvoll, L.-L. Ching, T. A. Eberspacher, J. I. Brauman, J. W. Bacon, and L. H. Pignolet, Inorg. Chem., 1996, 35, 6746.

    Article  CAS  Google Scholar 

  74. K. Kohata, H. Higashio, Y. Yamaguchi, M. Koketsu, and T. Odashima, Bull. Chem. Soc. Jpn., 1994, 67, 668.

    Article  CAS  Google Scholar 

  75. H. Meier, Y. Kebuks, and S.-I. Kugimiga, J. Chem. Soc., Chem. Commun., 1989, 923.

  76. I. Tabushi and T. Sasaki, Tetrahedron Lett., 1982, 23, 1913.

    Article  CAS  Google Scholar 

  77. R. G. Little, J. Heterocycl. Chem., 1981, 18, 833.

    Article  CAS  Google Scholar 

  78. D. Hammel, C. Kautz, and K. Müllen, Chem. Ber., 1990, 123, 1353.

    Article  CAS  Google Scholar 

  79. R. G. Little, J. Heterocycl. Chem., 1981, 18, 129.

    CAS  Google Scholar 

  80. Z. Gross and I. Toledano, J. Org. Chem., 1994, 59, 8312.

    Article  CAS  Google Scholar 

  81. E. Rose, M. Soleithavoup, L. Christ-Tommasino, and G. Moreau, J. Org. Chem., 1998, 63, 2042.

    Article  CAS  Google Scholar 

  82. S. G. DiMagno, R. A. Williams, and M. J. Therien, J. Org. Chem., 1994, 59, 6943.

    Article  CAS  Google Scholar 

  83. G. Casiraghi, M. Cornia, F. Zanardi, G. Rassu, E. Ragg, and R. Bortolini, J. Org. Chem., 1994, 59, 1801.

    Article  CAS  Google Scholar 

  84. M. Cornia, S. Binacchi, T. Del Soldato, F. Zanardi, and G. Casiraghi, J. Org. Chem., 1995, 60, 4964.

    Article  CAS  Google Scholar 

  85. G. Casiraghi, M. Cornia, G. Rassu, C. Del Sante, and P. Spanu, Tetrahedron, 1992, 48, 5619.

    CAS  Google Scholar 

  86. D. Hammel, P. Erk, B. Schuler, J. Heinze, and K. Mullen, Adv. Mater., 1992, 4, 737.

    Article  CAS  Google Scholar 

  87. C.-H. Lee and J. S. Lindsey, Tetrahedron, 1994, 50, 11427.

    Google Scholar 

  88. T. Mizutani, T. Ema, T. Tomita, Y. Kuroda, and H. Ogoshi, J. Am. Chem. Soc., 1994, 116, 4240.

    Article  CAS  Google Scholar 

  89. N. Nishino, R. W. Wagner, and J. S. Lindsey, J. Org. Chem., 1996, 61, 7534.

    Article  CAS  Google Scholar 

  90. J. P. Nagarkatti and K. R. Ashley, Synthesis, 1974, 186.

  91. G. Shipps, Jr., and J. Rebek, Jr., Tetrahedron Lett., 1994, 35, 6823.

    Article  CAS  Google Scholar 

  92. B. Vaz, R. Alvarez, M. Nieto, A. I. Paniello, and A. R. DeLera, Tetrahedron Lett., 2001, 42, 7409.

    Article  CAS  Google Scholar 

  93. S. J. Vigmond, K. M. R. Kallury, and M. Thompson, Anal. Chem., 1992, 64, 2763.

    Article  CAS  Google Scholar 

  94. T. P. Wijesekera, Can. J. Chem., 1996, 74, 1868.

    Article  CAS  Google Scholar 

  95. C. Bruckner, E. D. Sternberg, R. W. Boyle, and D. Dolphin, Chem. Commun., 1997, 1689.

  96. I. M. Dixon and J.-P. Collin, J. Porphyrins Phthalocyanines, 2001, 5, No. 7, 600.

    Article  CAS  Google Scholar 

  97. Y. Suga, T. Arimura, S. Ide, T. Nishioka, H. Sugihara, S. Murata, and H. Tsuzuki, J. Chem. Res. Synop., 2000, No. 11, 512.

  98. G. R. Geier III, B. J. Littler, and J. S. Lindsey, J. Chem. Soc., Perkin Trans. 2, 2001, No. 5, 701.

  99. T. Akiyama, H. Imahori, A. Ajawakon, and Y. Sakata, Chem. Lett., 1996, 907.

  100. M. Ravikanth, J.-P. Strachan, F. Li, and J. S. Lindsey, Tetrahedron, 1998, 54, 7721.

    Article  CAS  Google Scholar 

  101. R. W. Wagner, T. E. Johnson, and J. S. Lindsey, J. Am. Chem. Soc., 1996, 118, 11166.

    Google Scholar 

  102. G. A. Baker, F. V. Bright, M. R. Detty, S. Pandey, C. E. Stilts, and H. Yao, J. Porphyrins Phthalocyanines, 2000, 4, No. 7, 669.

    Article  CAS  Google Scholar 

  103. E. N. Durantini, J. Porphyrins Phthalocyanines, 2000, 4, No. 3, 233.

    Article  CAS  Google Scholar 

  104. A. R. Genardy and D. Gabel, J. Porphyrins Phthalocyanines, 2002, 6, No. 6, 382.

    Google Scholar 

  105. J.-I. Setsune, M. Hashimoto, K. Shiozawa, J. Hayakawa, T. Ochi, and R. Masuda, Tetrahedron, 1998, 54, 1407.

    Article  CAS  Google Scholar 

  106. D. M. Wallace, S. H. Leung, M. O. Senge, and K. M. Smith, J. Org. Chem., 1993, 58, 7245.

    Article  CAS  Google Scholar 

  107. D. M. Wallace and K. M. Smith, Tetrahedron Lett., 1990, 31, 7265.

    Article  CAS  Google Scholar 

  108. C.-H. Lee, F. Li, K. Iwamoto, J. Dadok, A. A. Bothner-By, and J. S. Lindsey, Tetrahedron, 1995, 57, 11645.

    Google Scholar 

  109. M. Barbero, S. Cadamuro, L. Degani, R. Fochi, A. Gatti, and V. Regondi, J. Org. Chem., 1988, 53, 2245.

    Article  CAS  Google Scholar 

  110. M. Barbero, S. Cadamuro, I. Degani, R. Fochi, A. Gatti, and V. Regondi, Synthesis, 1986, 1074.

  111. J. L. Hoard, in Porphyrins and Metalloporphyrins, Ed. K. M. Smith, Elsevier, Amsterdam, 1975, Ch. 8, 317.

    Google Scholar 

  112. W. R. Scheidt, in The Porphyrins, Ed. D. Dolphin, Academic Press, New York, 1979, 3, Ch. 10, 463.

    Google Scholar 

  113. W. R. Scheidt and Y. Lee, J. Struct. Bonding (Berlin), 1987, 64, 1.

    CAS  Google Scholar 

  114. J. A. Shelnutt, X.-Z. Song, J.-G. Ma, S.-L. Jia, W. Jentzen, and C. J. Medforth, Chem. Soc. Rev., 1998, 27, 31.

    Article  CAS  Google Scholar 

  115. W. Jentzen, J.-G. Ma, and J. A. Shelnutt, Biophys J., 1998, 74, 753.

    Article  CAS  Google Scholar 

  116. J.-G. Ma, M. Laberge, X.-Z. Song, W. Jentzen, S.-L. Jia, J. Zhang, J. M. Vanderkooi, and J. A. Shelnutt, Biochem., 1998, 37, 5118.

    Article  CAS  Google Scholar 

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

    Google Scholar 

  118. B. Evans, K. M. Smith, and J.-H. Fuhrhop, Tetrahedron Lett., 1977, 443.

  119. K. M. Barkigia, M. D. Berber, J. Fajer, C. J. Medforth, M. W. Renner, and K. M. Smith, J. Am. Chem. Soc., 1990, 112, 8851.

    Article  CAS  Google Scholar 

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

  121. S. Ito, T. Murashima, H. Uno, and N. Ono, Chem. Commun., 1998, 1661.

  122. N. G. Kuz’min, A. S. Semeikin, and O. I. Koifman, USSR Pat. 1574603 (USSR); Byull. izobret., 1990, No. 24.

  123. T. D. Lash and P. Chandrasekar, J. Am. Chem. Soc., 1996, 118, 8767.

    Article  Google Scholar 

  124. C. J. Medforth, M. O. Senge, K. M. Smith, L. D. Sparks, and J. A. Shelnutt, J. Am. Chem. Soc., 1992, 114, 9859.

    Article  CAS  Google Scholar 

  125. J. Takeda and M. Sato, Chem. Pharm. Bull., 1994, 42, 1005.

    CAS  Google Scholar 

  126. T. Ema, M. O. Senge, N. Y. Nelson, H. Ogoshi, and K. M. Smith, Angew. Chem., Int. Ed. Engl., 1994, 33, 1879.

    Article  Google Scholar 

  127. W. Jentzen, M. C. Simpson, J. D. Hobbs, X. Song, T. Ema, N. Y. Nelson, C. J. Medforth, K. M. Smith, M. Veyrat, M. Mazzanti, R. Ramasseul, J.-C. Marchon, T. Takeuchi, W. A. Goddard III, and J. A. Shelnutt, J. Am. Chem. Soc., 1995, 117, 11085.

  128. M. O. Senge, L. Bischoff, N. Y. Nelson, and K. M. Smith, J. Porphyrins Phthalocyanines, 1999, 3, 99.

    Article  CAS  Google Scholar 

  129. J. A. Hodge, M. G. Hill, and H. B. Gray, Inorg. Chem., 1995, 34, 809.

    Article  CAS  Google Scholar 

  130. T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski, and R. Balasubramaniam, J. Org. Chem., 1992, 57, 4809.

    Article  CAS  Google Scholar 

  131. C. Bruckner, J. J. Posakony, C. K. Johnson, R. W. Boyle, B. R. James, and D. Dolphin, J. Porphyrins Phthalocyanines, 1998, 2, 455.

    Article  CAS  Google Scholar 

  132. R. Chong, P. S. Clezy, A. J. Liepa, and A. W. Nichol, Austral. J. Chem., 1969, 22, 229.

    Article  CAS  Google Scholar 

  133. S. J. Vigmond, M. C. Chang, K. M. R. Kallury, and M. Thompson, Tetrahedron Lett., 1994, 35, 2455.

    Article  CAS  Google Scholar 

  134. P. S. Clezy and G. A. Smithe, Austral. J. Chem., 1969, 22, 239.

    Article  CAS  Google Scholar 

  135. J. A. Ballantine, A. H. Jackson, G. W. Kenner, and G. McGillivray, Tetrahedron, Suppl. 7, 1966, 22, 241.

    Article  Google Scholar 

  136. K.-T. Oh, J.-W. Ka, J.-Y. Park, and C.-H. Lee, Bull. Kor. Chem. Soc., 1997, 18, 222.

    CAS  Google Scholar 

  137. Q. M. Wang and D. W. Bruce, Synlett., 1995, 1267.

  138. J. E. Baldwin, T. Klose, and M. K. Peters, J. Chem. Soc., Chem. Commun., 1976, 881.

  139. C. K. Chang and I. Abdalmuhdi, J. Org. Chem., 1983, 48, 5388.

    Article  CAS  Google Scholar 

  140. A. R. Battersby, E. Hunt, E. McDonald, J. B. Paine III, and J. Saunders, J. Chem. Soc., Perkin Trans. 1, 1976, 1008.

  141. A. R. Battersby, E. Hunt, M. Ihara, E. McDonald, J. B. Paine III, F. Satoh, and J. Saunders, J. Chem. Soc., Chem. Commun., 1974, 994.

  142. J. Almog, J. E. Baldwin, R. L. Dyer, and M. Peters, J. Am. Chem. Soc., 1975, 97, 226.

    Article  CAS  Google Scholar 

  143. A. S. Semeikin, S. A. Syrbu, T. V. Lyubimova, Zhurn. obshch. khimii, 2001, 71, 1747 [Russ. J. Gen. Chem., 2001, 71 (Engl. Transl.)].

    Google Scholar 

  144. H. Fischer and H. Orth, Justus Liebigs Ann. Chem., 1931, 489, 62.

    Article  CAS  Google Scholar 

  145. A. F. Mironov, T. R. Ovsepyan, R. P. Evstigneeva, and N. A. Preobrazhenskii, Zh. Obshch. Khim., 1975, 35, 324 [J. Gen. Chem. USSR, 1975, 35 (Engl. Transl.)].

    Google Scholar 

  146. H. Ogoshi, H. Sugimoto, T. Nishiguchi, T. Watanabe, Y. Matsuda, and Z.-I. Yoshida, Chem. Lett., 1978, 29.

  147. M. J. Gunter and L. N. Mander, J. Org. Chem., 1981, 46, 4792.

    Article  CAS  Google Scholar 

  148. Y. Aoyama, T. Kamohara, A. Yamagishi, H. Toi, and H. Ogoshi, Tetrahedron Lett., 1987, 28, 2143.

    Article  CAS  Google Scholar 

  149. M. J. Gunter and B. C. Robinson, Austral. J. Chem., 1990, 43, 1839.

    Article  CAS  Google Scholar 

  150. G. Li, S. Wu, and Y. Te, Youji Huaxue., 1985, No. 4, 300.

  151. R. Young and C. K. Chang, J. Am. Chem. Soc., 1985, 107, 898.

    Article  CAS  Google Scholar 

  152. A. S. Semeikin, T. V. Lyubimova, and O. A. Golubchikov, Zh. Prikl. Khim., 1993, 66, 710 [Russ. J. Appl. Chem., 1993, 66 (Engl. Transl.)].

    CAS  Google Scholar 

  153. J. L. Sessler, V. L. Capuano, and A. Harriman, J. Am. Chem. Soc., 1993, 115, 4618.

    Article  CAS  Google Scholar 

  154. J. I. Bruce, J.-C. Chambron, P. Kolle, and J.-P. Sauvage, J. Chem. Soc., Perkin Trans. 1, 2002, 1226.

  155. A. Osuka, B.-L. Liu, and K. Maruyama, J. Org. Chem., 1993, 58, 3582.

    Article  CAS  Google Scholar 

  156. J. L. Sessler, B. Wang, and A. Harriman, J. Am. Chem. Soc., 1995, 117, 704.

    Article  CAS  Google Scholar 

  157. M. R. Wasielewski, M. P. Niemezyk, W. A. Svec, and E. B. Pewitt, J. Am. Chem. Soc., 1985, 107, 5562.

    Article  CAS  Google Scholar 

  158. M. R. Wasielewski, G. L. Gaines III, M. P. O’Neil, W. A. Svec, and M. P. Niemezyk, J. Am. Chem. Soc., 1990, 112, 4559.

    Article  CAS  Google Scholar 

  159. M. R. Wasielewski, D. G. Johnson, M. P. Niemezyk, G. L. Gaines III, M. P. O’Neil, and W. A. Svec, J. Am. Chem. Soc., 1990, 112, 6482.

    Article  CAS  Google Scholar 

  160. A. Osuka, H. Yamada, K. Maruyama, N. Mataga, T. Asahi, M. Ohkouchi, T. Okada, I. Yamazaki, and Y. Nishimura, J. Am. Chem. Soc., 1993, 115, 9439.

    Article  CAS  Google Scholar 

  161. M. Ohkohchi, A. Takahashi, N. Mataga, T. Okada, A. Osuka, H. Yamada, and K. Maruyama, J. Am. Chem. Soc., 1993, 115, 12137.

    Google Scholar 

  162. N. Zh. Mamardashvili, A. S. Semeikin, and O. A. Golubchikov, Zh. Org. Khim., 1993, 29, 1213 [Russ. J. Org. Chem., 1993, 29 (Engl. Transl.)].

    CAS  Google Scholar 

  163. J. E. Baldwin, M. J. Crossley, T. Klose, E. A. O’Rear III, and M. K. Peters, Tetrahedron, 1982, 38, 27.

    Article  CAS  Google Scholar 

  164. J. P. Collman, A. O. Chong, G. B. Jameson, R. T. Oakley, E. Rose, E. R. Schmittou, and J. A. Ibers, J. Am. Chem. Soc., 1981, 103, 516.

    Article  CAS  Google Scholar 

  165. A. Lecas, J. Levisalles, Z. Renko, and E. Rose, Tetrahedron Lett., 1984, 25, 1563.

    Article  CAS  Google Scholar 

  166. K. Maruyama, T. Nagata, and T. Osuka, J. Phys. Org. Chem., 1988, 1, 63.

    Article  CAS  Google Scholar 

  167. M. O. Senge, C. J. Medforth, T. P. Forsyth, D. A. Lee, M. M. Olmstead, W. Jehtzen, R. K. Pandey, J. A. Shelnutt, and K. M. Smith, Inorg. Chem., 1997, 36, 1149.

    Article  CAS  Google Scholar 

  168. H. Tamiaki, A. Kiyomori, and K. Maruyama, Bull. Chem. Soc. Jpn., 1994, 67, 2478.

    Article  CAS  Google Scholar 

  169. N. Zh. Mamardashvili, O. A. Golubchikov, G. M. Mamardashvili, and W. Dehaen, J. Porphyrins Phthalocyanines, 2002, 6, 476.

    Article  CAS  Google Scholar 

  170. D. Wöhrle, Macromol. Rapid Commun., 2001, 22, 68.

    Article  Google Scholar 

  171. N. G. Kuz’min, Ph.D. Thesis (chem.), Ivanovo Institute for Chemical Technology, Ivanovo, 1990 (in Russian).

  172. I. Abdalmuhdi and C. K. Chahg, J. Org. Chem., 1985, 50, 411.

    Article  CAS  Google Scholar 

  173. J. P. Collman, J. E. Hutchison, M. A. Lopez, A. Tabard, R. Guilard, W. K. Seok, J. A. Ibers, and M. L’Her, J. Am. Chem. Soc., 1992, 114, 9869.

    Article  CAS  Google Scholar 

  174. R. Guilard, M. A. Lopes, A. Tabard, P. Richard, C. Lecomte, S. Brandes, J. E. Hutchisan, and J. P. Collman, J. Am. Chem. Soc., 1992, 114, 9877.

    Article  CAS  Google Scholar 

  175. D. Heiler, G. Mc Lendon, and P. Rogalskyj, J. Am. Chem. Soc., 1987, 109, 604.

    Article  CAS  Google Scholar 

  176. A. Osuka and K. Maruyama, Chem. Lett., 1987, 825.

  177. A. Osuka and K. Maruyama, J. Am. Chem. Soc., 1988, 110, 4454.

    Article  CAS  Google Scholar 

  178. A. Osuka, K. Maruyama, I. Yamazaki, and N. Tamai, J. Chem. Soc., Chem. Commun., 1988, 1243.

  179. A. Osuka, K. Ida, and K. Meruyama, Chem. Lett., 1989, 741.

  180. A. Osuka, H. Tomita, and K. Meruyama, Chem. Lett., 1988, 1205.

  181. J. L. Sessler and S. Pierind, Tetrahedron Lett., 1987, 28, 6569.

    Article  CAS  Google Scholar 

  182. J. L. Sessler and M. R. Johnson, Angev. Chem., 1987, 99, 679.

    Article  CAS  Google Scholar 

  183. P. S. Clezy, C. J. R. Fookes, and A. J. Liepa, Austral. J. Chem., 1972, 25, 1979.

    Article  CAS  Google Scholar 

  184. D. Karris, A. W. Johnson, and R. Caete-Holmes, Bioorg. Chem., 1980, 9, 63.

    Article  Google Scholar 

  185. A. M. Shul’ga and G. P. Gurinovich, Dokl. Akad. Nauk BSSR [Bull. Bellorussian Acad. Sci.], 1981, 25, 55 (in Russian).

  186. D. Dolphin, A. W. Johnson, J. Zeng, and P. Brock van der, J. Chem. Soc., 1966, 880.

  187. A. W. Johnson and I. T. Kay, J. Chem. Soc., 1965, 1620.

  188. V. I. Mel’nik, Ph.D. Thesis (chem.), A. V. Bogatsky Physico-chemical Institute, Ukrainian National Academy of Sciences, Odessa. 1979. 21 pp. (in Russian).

  189. A. S. Semeikin, O. I. Koifman, B. D. Berezin, and S. A. Syrbu, Khim. Geterotsikl. Soedinen., 1983, 1359 [Chem. Heterocycl. Compd., 1983, No. 10 (Engl. Transl.)].

  190. L. R. Mildrom, J. Chem. Soc., Perkin. Trans. 1, 1983, 2535.

  191. A. C. Chan, J. Dalton, and L. R. Mildrom, J. Chem. Soc., Perkin. Trans. 2, 1982, 707.

  192. J. Dalton and L. R. Mildrom, J. Chem. Soc., Chem. Commun., 1979, 609.

  193. E. Tsuchida, E. Hasegava, T. Komatsu, T. Nakata, and H. Nishide, Chem. Lett., 1990, 389.

  194. S. Matile, T. Hansen, A. Storster, and W. D. Wogjon, Helv. Chim Acta, 1994, 77, 1087.

    Article  CAS  Google Scholar 

  195. M. Momenteau, Le F. Bras, and B. Looch, Tetrahedron Lett., 1994, 35, 3289.

    Article  CAS  Google Scholar 

  196. S. A. Syrbu, A. S. Semeikin, and B. D. Berezin, USSR Pat. 1684284 (USSR); Byull. izobret., 1991, No. 38.

  197. S. A. Syrbu and A. S. Semeikin, Zh. Org. Khim., 1999, 35, 1262 [Russ. J. Org. Chem., 1999, 35 (Engl. Transl.)].

    Google Scholar 

  198. R. G. Little, J. Heterocycl. Chem., 1978, 15, 203.

    CAS  Google Scholar 

  199. M. Momenteau and B. Loock, J. Mol. Catal., 1980, 7, 315.

    Article  CAS  Google Scholar 

  200. A. S. Semeikin, O. I. Koifman, G. E. Nikitina, and B. D. Berezin, Zh. Org. Khim., 1984, 54, 1599 [J. Org. Chem. USSR, 1984, 54 (Engl. Transl.)].

    CAS  Google Scholar 

  201. B. D. Berezin, A. S. Semeikin, G. E. Nikitina, Z. Ts. Koifman, and O. I. Koifman, Zh. Fiz. Khim., 1985, 59, 2226 [Russ. J. Phys. Chem., 1985, 59 (Engl. Transl.)].

    CAS  Google Scholar 

  202. S. A. Syrbu, A. S. Semeikin, B. D. Berezin, and O. I. Koifman, Khim. Geterotsikl. Soedinen., 1989, 1373 [Chem. Heterocycl. Compd., 1989, No. 10 (Engl. Transl.)].

  203. Techniques and Topics in Bioinorganic Chemistry, Ed. C. A. McAnliffe, University of Manchester, Institute of Science and Technology, 1975.

  204. L. Ding, G. Etemad-Moghadam, S. Cros, C. Auclair, and B. Meunier, J. Med. Chem., 1991, 34, 900.

    Article  CAS  Google Scholar 

  205. P. Kus, G. Knerr, and L. Gzuchajowski, Tetrahedron Lett., 1990, 31, 5133.

    Article  CAS  Google Scholar 

  206. X. Jiang, P. K. Pandey, and K. M. Smith, J. Chem. Soc., Perkin. Trans. 1, 1996, 1607.

  207. S. A. Syrbu, A. S. Semeikin, B. D. Berezin, and O. I. Koifman, Khimiya Geterotsikl. Soedinen., 1987, 781 [Chem. Heterocycl. Compd., 1987, No. 8 (Engl. Transl.)].

  208. J. P. Collman, R. R. Gagne, T. R. Halbert, J. C. Marchon, and C. A. Reed, J. Am. Chem. Soc., 1973, 95, 7868.

    Article  CAS  Google Scholar 

  209. A. S. Semeikin, O. I. Koifman, and B. D. Berezin, Khim. Geterotsikl. Soedinen., 1982, 1354 [Chem. Heterocycl. Compd., 1982, No. 10 (Engl. Transl.)].

  210. A. S. Semeikin, O. I. Koifman, and B. D. Berezin, Izv. Vuzov. Khim. Khim. Tekhnol., 1985, 28, No. 11, 47 [Izv. Vuz. Khim. Khim. Tekhnol., 1985, 28, No. 11 (Engl. Transl.)].

    CAS  Google Scholar 

  211. F. Tang, L. Wang, and Z. Chai, Chem. Reagents, 1993, 15, 324.

    CAS  Google Scholar 

  212. X. Wu, Z. Chen, and Z. Ziang, J. Wunan Univ. Natir. Sci. Ed., 1993, No. 4, 30.

  213. S. E. Gribkova, V. N. Luzgina, and R. P. Evstigneeva, Zh. Org. Khim., 1993, 29, 758 [Russ. J. Org. Chem., 1993, 29 (Engl. Transl.)].

    CAS  Google Scholar 

  214. A. Palka and L. Czuchajowski, Chem. Lett., 1994, 547.

  215. S. A. Syrbu, A. V. Glazunov, and A. S. Semeikin, Izv. Vuzov. Khim. Khim. Tekhnol., 2006, 49, No. 4, 102 [Izv. Vuz. Khim. Khim. Tekhnol., 2006, 49, No. 4 (Engl. Transl.)].

    Google Scholar 

  216. O. I. Nikolaeva, S. S. Kurek, T. A. Ageeva, and O. I. Koifman, Izv. Vuzov. Khim. Khim. Tekhnol., 2004, 47, No. 2, 46 [Izv. Vuz. Khim. Khim. Tekhnol., 2004, 47, No. 2 (Engl. Transl.)].

    Google Scholar 

  217. D. V. Belykh, O. I. Nikolaeva, T. A. Ageeva, I. A. Vershinina, L. P. Karmanova, and A. V. Kuchin, Izv. Vuzov. Khim. Khim. Tekhnol., 2004, 47, No. 5, 102 [Izv. Vuz. Khim. Khim. Tekhnol., 2004, 47, No. 5 (Engl. Transl.)].

    CAS  Google Scholar 

  218. O. I. Nikolaeva, T. A. Ageeva, O. I. Koifman, and S. S. Kurek, Plastmassy so spetsial’nymi svoistvami: tekhnologii I primenenie [Plastics with Special Properties: Processing and Applications], in Collection of Works of SPbGTI(TU), St.-Peterburg, 2004, 47 (in Russian).

  219. O. I. Nikolaeva, S. S. Kurek, T. A. Ageeva, A. S. Semeykin, and O. I. Koifman, J. Porphyrins Phthalocyanines, 2004, 8, No. 4–6, 587.

    Google Scholar 

  220. A. B. Solov’eva, A. I. Samokhvalova, T. S. Lebedeva, V. S. Pshezhetskii, L. V. Karmilova, and N. S. Enikolopyan, Dokl. Akad. Nauk SSSR, 1986, 290, 1383 [Dokl. Chem., 1986 (Engl. Transl.)].

    CAS  Google Scholar 

  221. A. B. Solovieva, E. A. Lukashova, A. Vorobiev, and S. F. Timashev, Reactive Polymers, 1991/1992, 16, 9.

    Article  Google Scholar 

  222. E. J. Tsuchida, Macromol. Sci. Chem., A, 1979, 13, 545.

    Article  Google Scholar 

  223. E. Tsuchida, Polym. J., 1978, 14, 123.

    Google Scholar 

  224. E. Tsuchida, F. Hasegawa, and T. Kanayama, Macromolecules, 1978, 11, 947.

    Article  CAS  Google Scholar 

  225. E. Hasegawa, T. Kanayama, and E. Tsuchida, Polym. Sci., Polym. Chem. Ed., 1977, 15, 3039.

    Article  CAS  Google Scholar 

  226. E. Tsuchida, H. Nishide, M. Yuasa, E. Hasegawa, K. Eshima, and Y. Matsushita, Macromolecules, 1989, 22, 2103.

    Article  CAS  Google Scholar 

  227. H. Nishide, M. Yuasa, E. Hasegawa, and E. Tsuchida, Macromolecules, 1987, 20, 1913.

    Article  CAS  Google Scholar 

  228. H. Hiroyoshi, T. Nakata, and S. Komatsu, Bull. Chem. Soc. Jpn., 1991, 64, 2300.

    Article  Google Scholar 

  229. E. Tsuchida, H. Nishide, E. Hasegawa, and Y. Matsushita, J. Chem. Soc., Dalton Trans., 1984, 1147.

  230. E. Tsuchida and H. Nishide, Top. Curr. Chem., 1986, 132, 63.

    Article  CAS  Google Scholar 

  231. G. A. Zhamkochan, M. E. Akopyan, L. M. Akopyan, and T. S. Kurtikyan, Khim. Geterotsikl. Soedinen., 1987, 221 [Chem. Heterocycl. Compd., 1987, No. 2 (Engl. Transl.)].

  232. V. F. Razumov, A. G. Ivanchenko, A. D. Pomogailo, I. S. Voloshanovskii, and A. I. Kuzaev, Vysokomolekulyar. Soedineniya, Ser. B, 1997, 39, 2046 [Polym. Sci., Ser. B, 1997, 39, No. 12 (Engl. Transl.)].

    CAS  Google Scholar 

  233. A. D. Pomogailo, V. F. Razumov, and I. S. Voloshaovskii, J. Porphyrins Phthalocyanines, 2000, 4, 45.

    Article  CAS  Google Scholar 

  234. A. D. Pomogailo, N. M. Bravaya, V. F. Razumov, and I. S. Voloshanovskii, Izv. Akad. Nauk. Ser. Khim., 1996, 2922 [Russ. Chem. Bull., 1996, 45, 2773 (Engl. Transl.)].

    Google Scholar 

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 680–703, April, 2007.

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Syrbu, S.A., Ageeva, T.A., Semeikin, A.S. et al. Synthesis of meso-phenyl-substituted porphyrins as starting compounds for the preparation of porphyrin-containing polymers. Russ Chem Bull 56, 707–731 (2007). https://doi.org/10.1007/s11172-007-0108-y

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