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Porphyrin-Calix[4]arenes

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Abstract

The review deals with the synthesis, chemical modification, and complexing properties of a new class of molecular receptors, porphyrin-calix[4]arene conjugates.

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REFERENCES

  1. Antipin, I.S., Kazakov, E.Kh., Habicher, W.D., and Konovalov, A.I., Usp. Khim., 1998, vol. 67, p. 995.

    Google Scholar 

  2. Rudkevich, D.M., Verboom, W., and Reinhoudt, D., Tetrahedron Lett., 1994, vol. 35, p. 7131.

    Article  Google Scholar 

  3. Cram, D.J., Angew. Chem., Int. Ed. Engl., 1988, vol. 27, p. 1009.

    Google Scholar 

  4. Lehn, J.-M., Angew. Chem., Int. Ed. Engl., 1990, vol. 29, p. 1304.

    Google Scholar 

  5. Berezin, B.D. and Enikolopyan, N.S., Metalloporfiriny (Porphyrin Metal Complexes), Moscow: Nauka, 1988, p. 158.

    Google Scholar 

  6. Mamardashvili, N.Zh. and Golubchikov, O.A., Usp. Khim., 2000, vol. 69, p. 337.

    Google Scholar 

  7. Mamardashvili, N.Zh. and Golubchikov, O.A., Rus. Chem. Rev., 2001, vol. 70, p. 577.

    Article  Google Scholar 

  8. Bohmer, V., Angew. Chem., Int. Ed. Engl., 1995, vol. 34, p. 713.

    Google Scholar 

  9. Ikeda, A. and Shinkai, S., Chem. Rev., 1997, vol. 97, p. 1713.

    PubMed  Google Scholar 

  10. Anderson, S., Anderson, H.L., and Sanders, J.K.M., Acc. Chem. Res., 1993, vol. 26, p. 469.

    Article  Google Scholar 

  11. Pochini, A. and Ungaro, R., Comprehensive Supramolecular Chemistry, Oxford: Pergamon, 1996, vol. 2, p. 103.

    Google Scholar 

  12. McKervery, M.A., Schwing-Weill, M.J., and Arnaud-Neu, F., Comprehensive Supramolecular Chemistry, Oxford: Pergamon, 1996, vol. 1, p. 537.

    Google Scholar 

  13. Van Loon, J.-D., Verboom, W., and Reinhoudt, D.N., Org. Prep. Proced. Int., 1992, vol. 24, p. 437.

    Google Scholar 

  14. Hamilton, A., Lehn, J.M., and Sessler, J.L., Chem. Commun., 1984, p. 311.

  15. Hamilton, A., Lehn, J.M., and Sessler, J.L., J. Am. Chem. Soc., 1986, vol. 108, p. 5158.

    Article  Google Scholar 

  16. Kuroda, Y., Hiroshige, T., and Ogoshi, H., Chem. Commun., 1990, p. 1594.

  17. Weber, L., Imiolczyk, I., Haufe, G., Rehorek, D., and Hennig, H., Chem. Commun., 1992, p. 301.

  18. Kuroda, Y., Sera, T., and Ogoshi, H., J. Am. Chem. Soc., 1991, vol. 113, p. 2793.

    Article  Google Scholar 

  19. Middle, O., Verboom, W., and Reinhoudt, D.N., J. Org. Chem., 2001, vol. 66, p. 3998.

    Article  PubMed  Google Scholar 

  20. Fiammengo, R., Timmerman, P., de Jong, F., and Reinhoudt, D.N., Chem. Commun., 2000, p. 2313.

  21. Nagasaki, T., Fujishima, H., Takeuchi, M., and Shinkai, S., J. Chem. Soc., Perkin Trans. 1, 1995, p. 1883.

  22. Arimura, T., Ide, S., Sugihara, H., Murata, S., and Sessler, J.L., New J. Chem., 1999, vol. 23, p. 977.

    Article  Google Scholar 

  23. Takahashi, K., Gunji, A., Guillaumont, D., Pichierri, F., and Nakamura, S., Angew. Chem., Int. Ed., 2000, vol. 39, p. 2925.

    Google Scholar 

  24. Arimura, T., Ide, S., Sugihara, H., Murata, S., and Sato, M., J. Jpn. Oil Chem. Soc., 1999, vol. 48, p. 775.

    Google Scholar 

  25. Hynes, M., J. Chem. Soc., Dalton Trans., 1993, p. 311.

  26. Whitlock, B.J. and Whitlock, H.W., Jr., J. Am. Chem. Soc., 1990, vol. 112, p. 3910.

    Article  Google Scholar 

  27. Arimura, T., Ide, S., Suga, Y., Nishioka, T., Murata, S., Tachiya, M., Nagamura, T., and Inoue, H., J. Am. Chem. Soc., 2001, vol. 123, p. 10 744.

    Article  Google Scholar 

  28. Middel, O., Verboom, W., and Reinhoudt, D.N., J. Org. Chem., 2001, vol. 66, p. 3998.

    Article  PubMed  Google Scholar 

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

    Article  Google Scholar 

  30. Lindsey, J.S., Schreiman, I.C., Hsu, H.C., Kearney, P.C., and Marguerettaz, A.M., J. Org. Chem., 1987, vol. 52, p. 827.

    Article  Google Scholar 

  31. Deviprasad, G.R. and D’Souza, F., Chem. Commun., 2000, p. 1915.

  32. Kobayashi, N., Mizuno, K., and Osa, T., Inorg. Chim. Acta, 1994, vol. 224, p. 1.

    Article  Google Scholar 

  33. Almog, J., Baldwin, J.E., Dyer, R.L., and Peters, M., J. Am. Chem. Soc., 1977, vol. 99, p. 2819.

    Article  PubMed  Google Scholar 

  34. Shinkai, S., Arimura, T., Kawabata, H., Murakami, H., Araki, K., Iwamoto, K., and Matsuda, T., Chem. Commun., 1990, p. 1734.

  35. Wasielewski, M.R., Chem. Rev., 1992, vol. 92, p. 435.

    Article  Google Scholar 

  36. Milbradt, R. and Weiss, J., Tetrahedron Lett., 1995, vol. 36, p. 2999.

    Article  Google Scholar 

  37. Manka, S.J. and Lawrence, D.S., Tetrahedron Lett., 1989, vol. 30, p. 6889.

    Google Scholar 

  38. Momenteau, M., Mispelter, J., Loock, B., and Bisagni, E., J. Chem. Soc., Perkin Trans. 1, 1983, p. 189.

  39. Momenteau, M., Pure Appl. Chem., 1986, vol. 58, p. 1493.

    Google Scholar 

  40. Crossley, M.J., Field, L.D., Foster, A.J., Harding, M.M., and Sternhell, S., J. Am. Chem. Soc., 1987, vol. 109, p. 341.

    Article  Google Scholar 

  41. Cobben, P.L.H.M., Egberink, R.J.M., Bomer, J.G., Bergveld, P., Verboom, W., and Reinhoudt, D.N., J. Am. Chem. Soc., 1992, vol. 114, p. 10 573.

    Article  Google Scholar 

  42. Brzozka, Z., Lammerink, B., Reinhoudt, D.N., Ghidini, E., and Ungaro, R.J., Chem. Soc., Perkin Trans. 2, 1993, p. 1037.

  43. Morzherin, Y., Rudkevich, D.M., Verboom, W., and Reinhoudt, D.N., J. Org. Chem., 1993, vol. 58, p. 7602.

    Article  Google Scholar 

  44. Iwema-Bakker, W.I., Haas, M., Khoo-Beattie, C., Ostaszewski, R., Franken, S.M., den Hertog, H.J., Jr., Verboom, W., de Zeeuw, D., Harkema, S., and Reinhoudt, D.N., J. Am. Chem. Soc., 1994, vol. 116, p. 123.

    Article  Google Scholar 

  45. van Loon, J.-D., Janssen, R.G., Verboom, W., and Reinhoudt, D.N., Tetrahedron Lett., 1992, vol. 33, p. 5125.

    Article  Google Scholar 

  46. Reichwein, A.M., Verboom, W., Harkema, S., Spek, A.L., and Reinhoudt, D.N., J. Chem. Soc., Perkin Trans. 2, 1994, p. 1167.

  47. Kuroda, Y. and Ogoshi, H., Synlett, 1994, p. 319.

  48. Danks, I.P., Sutherland, I.O., and Hong Yap, C., J. Chem. Soc., Perkin Trans. 1, 1990, p. 421.

  49. Mackay, L.G., Wylie, R.S., and Sanders, J.K.M., J. Am. Chem. Soc., 1994, vol. 116, p. 3141.

    Article  Google Scholar 

  50. Bonar-Law, R.P. and Sanders, J.K.M., Chem. Commun., 1991, p. 574.

  51. Asfari, Z., Vicens, J., and Weiss, J., Tetrahedron Lett., 1993, vol. 34, p. 627.

    Article  Google Scholar 

  52. Dudic, M., Lhotak, P., Petrickova, H., Stibor, I., Lang, K., and Sykora, J., Tetrahedron, 2003, vol. 59, p. 2409.

    Article  Google Scholar 

  53. Kumagai, H., Hasegawa, M., Miyanari, S., Sugawa, Y., Sato, Y., Hori, T., Ueda, S., Kamiyama, H., and Miyano, S., Tetrahedron Lett., 1997, vol. 38, p. 3971.

    Article  Google Scholar 

  54. Iki, N., Kabuto, C., Fukushima, T., Kumagai, H., Takeya, H., Miyanari, S., Miyashi, T., and Miyano, S., Tetrahedron, 2000, vol. 56, p. 1437.

    Article  Google Scholar 

  55. Dudic, M., Lhotak, P., Stibor, I., Dvorakova, H., and Lang, K., Tetrahedron, 2002, vol. 58, p. 5475.

    Article  Google Scholar 

  56. Gouterman, M., The Porphyrins, New York: Academic, 1978, vol. 3, p. 1.

    Google Scholar 

  57. Nappa, N. and Valentine, J.S., J. Am. Chem. Soc., 1978, vol. 100, p. 5075.

    Article  Google Scholar 

  58. Chang, C.J., Deng, Y., Heyduk, A.F., Chang, C.K., and Nocera, D.G., Inorg. Chem., 2000, vol. 39, p. 959.

    Article  PubMed  Google Scholar 

  59. Fletcher, J.T. and Therien, M.J., J. Am. Chem. Soc., 2002, vol. 124, p. 4298.

    Article  PubMed  Google Scholar 

  60. Nataga, T., Osuka, A., and Maruyama, K., J. Am. Chem. Soc., 1990, vol. 112, p. 3054.

    Article  Google Scholar 

  61. Taylor, P.N. and Anderson, H.L., J. Am. Chem. Soc., 1999, vol. 121, p. 11 538.

    Google Scholar 

  62. Kasha, M., Rawls, H.R., and El-Bayoumi, M.A., Pure Appl. Chem., 1965, vol. 11, p. 371.

    Google Scholar 

  63. Lhotak, P., St’astny, V., Zlatuskova, P., Stibor, I., Michlova, V., Tkadlecova, M., Havlicek, J., and Sykora, J., Collect. Czech. Chem. Commun., 2000, vol. 65, p. 757.

    Article  Google Scholar 

  64. Lhotak, P., Himl, M. Pakhomova, S., and Stibor, I., Tetrahedron Lett., 1998, vol. 39, p. 8915.

    Article  Google Scholar 

  65. Lhotak, P., Kaplanek, L., Stibor, I., Lang, J., Dvorakova, H., Hrabal, R., and Sykora, J., Tetrahedron Lett., 2000, vol. 41, p. 9339.

    Article  Google Scholar 

  66. Lang, J., Dvorakova, H., Bartosova, I., Lhotak, P., Stibor, I., and Hrabal, R., Tetrahedron Lett., 1999, vol. 40, p. 373.

    Article  Google Scholar 

  67. Lang, J., Vlach, J., Dvorakova, H., Lhotak, P., Himl, M., Hrabal, R., and Stibor, I., J. Chem. Soc., Perkin Trans. 2, 2001, p. 576.

  68. Lhotak, P., Dudic, M., Stibor, I., Petrickova, H., Sykora, J., and Hodacova, J., Chem. Commun., 2001, p. 731.

  69. Gutsche, C.D., Host Guest Complex Chemistry: Macrocycles: Synthesis, Structures, Applications, Vogtle, F. and Weber, E., Eds., Berlin: Springer, 1985. Translated under the title Khimiya kompleksov “gost’-khozyain.” Sintez, struktury i primenenie, Moscow: Mir, 1988, p. 445.

    Google Scholar 

  70. Gutsche, C.D., Calixarenes. Monographs in Supramolecular Chemistry, Stoddart, J.F., Ed., Cambridge: The Royal Society of Chemistry, 1989, p. 224.

    Google Scholar 

  71. Gutsche, C.D., Calixarenes Revisited. Monographs in Supramolecular Chemistry, Stoddart, J.F., Cambridge: The Royal Society of Chemistry, 1998, p. 236.

    Google Scholar 

  72. Hosseini, M.W., Calixarenes for Separations, Lumetta, G.J., Rogers, R.D., and Gopalan, A.S., Eds., Washington, DC: Am. Chem. Soc., 2000, ACS Symposium Series vol. 757, p. 296.

    Google Scholar 

  73. Beer, P.D., Chem. Commun., 1996, p. 689.

  74. Scheerder, J., Fochi, M., Engbersen, J.F.J., and Reinhoudt, D.N., J. Org. Chem., 1994, vol. 59, p. 7815.

    Article  Google Scholar 

  75. Scheerder, J., Engbersen, J.F.J., Casnati, A., Ungaro, R., and Reinhoudt, D.N., J. Org. Chem., 1995, vol. 60, p. 6448.

    Article  Google Scholar 

  76. Scheerder, J., van Duynhoven, J.P.M., Engbersen, J.F.J., and Reinhoudt, D.N., Angew. Chem., Int. Ed. Engl., 1996, vol. 35, p. 1090.

    Google Scholar 

  77. Pelizzi, N., Casnati, A., Friggeri, A., and Ungaro, R., Chem. Commun., 1998, p. 1307.

  78. Nam, K.Ch., Kang, S.O., Jeong, H.S., and Jeon, S., Tetrahedron Lett., 1999, vol. 40, p. 7343.

    Article  Google Scholar 

  79. Budka, J., Lhotak, P., Michlova, V., and Stibor, I., Tetrahedron Lett., 2001, vol. 42, p. 1583.

    Article  Google Scholar 

  80. Stastny, V., Lhotak, P., Michlova, V., Stibor, I., and Sykora, J., Tetrahedron, 2002, vol. 58, p. 7207.

    Article  Google Scholar 

  81. Shimizu, K.D. and Rebek, J., Proc. Natl. Acad. Sci. USA, 1995, vol. 92, p. 12 403.

    Google Scholar 

  82. Mogck, O., Bohmer, V., and Vogt, W., Tetrahedron, 1996, vol. 52, p. 8489.

    Article  Google Scholar 

  83. Dudic, M., Lhotak, P., Stibor, I., Lang, K., and Proskova, P., Org. Lett., 2003, vol. 5, p. 149.

    Article  PubMed  Google Scholar 

  84. Van Wagenningen, A.M., Snip, E., Verboom, W., Reinhoudt, D.N., and Boerrigter, H., Justus Liebigs Ann. Chem., 1997, p. 2235.

  85. Li, D.M., Zhao, Z.X., Liu, S.Q., Liu, G.F., Shi, T.S., and Liu, X.X., Synth. Commun., 2000, vol. 30, p. 4017.

    Google Scholar 

  86. Tsuchida, E., Hasegawa, E., and Kanayama, T., Macromolecules, 1978, vol. 11, p. 947.

    Article  Google Scholar 

  87. Collman, J.P., Wang, Z., and Straumanis, A., J. Org. Chem., 1998, vol. 63, p. 2424.

    Article  PubMed  Google Scholar 

  88. Jokic, D., Asfari, Z., and Weiss, J., Org. Lett., 2002, vol. 4, p. 2129.

    Article  PubMed  Google Scholar 

  89. Klenke, B. and Friederichsen, W., J. Chem. Soc., Perkin Trans. 1, 1998, p. 3377.

  90. Yam, V.W.W., Cheung, K.L., Yuan, L.H., Wong, K.M.C., and Cheung, K.K., Chem. Commun., 2000, p. 1513.

  91. Mamardashvili, N.Zh., Golubchikov, O.A., Pognon, G., and Weiss, J., Abstracts Book of IXth Int. Conf. on Porphyrin Chemistry, Suzdal, Russia, 2003, p. 86.

  92. Mori, A., Mohamed Ahmed, M.S., Sekiguchi, A., Masui, K., and Koike, T., Chem. Lett., 2002, p. 756.

  93. Arnold, D.P. and Hartnell, R.D., Tetrahedron, 2001, vol. 57, p. 1335.

    Article  Google Scholar 

  94. Arnold, D., Johnson, A.W., and Mahedran, M., J. Chem. Soc., Perkin Trans. 1, 1978, p. 366.

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  1. Institute of Solution Chemistry, Russian Academy of Sciences, ul. Akademicheskaya 1, Ivanovo, 153045, Russia

    N. Zh. Mamardashvili & O. I. Koifman

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  1. N. Zh. Mamardashvili
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 6, 2005, pp. 807–826.

Original Russian Text Copyright © 2005 by Mamardashvili, Koifman.

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Mamardashvili, N.Z., Koifman, O.I. Porphyrin-Calix[4]arenes. Russ J Org Chem 41, 787–806 (2005). https://doi.org/10.1007/s11178-005-0247-2

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