Skip to main content
Log in

Fullerene-containing porphyrins: Synthesis and potential practical applications

  • Selected articles originally published in Russian in Rossiiskii Khimicheskii Zhurnal (Russian Chemistry Journal)
  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The review focuses current research in the rapidly developing field of the chemistry of porphyrin–fullerene complexes. Recent advances in the synthesis, properties, and potential applications of these compounds are considered. An overview of the most popular methods to prepare porphyrin complexes with C60 fullerene is given. The discussion of porphyrin‒fullerene complexes includes the structures of noncovalently linked porphyrin‒fullerenes along with covalently linked complexes. Much attention is paid to potential applications of porphyrin‒fullerene conjugates.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Kroto, H.W., Heath, J.R., O’Brien, S.C., Curl, R.F., and Smalley, R.E., Nature, 1985, vol. 318, no. 6042, p. 162.

    Article  CAS  Google Scholar 

  2. Yushkin, N.P., Dokl. Akad. Nauk, 1994, vol. 337, no. 6, p. 800.

    CAS  Google Scholar 

  3. Reznikov, V.A. and Polehovskii, Yu.S., Pis’ma v Zh. Tekh. Fiz., 2000, vol. 26, no. 15, p. 94.

    Google Scholar 

  4. Buseck, P.R., Earth Planet. Sci. Lett., 2002, vol. 203, no. 4. p. 781.

    Article  CAS  Google Scholar 

  5. Sidorov, L.N., Yurovskaya, M.A., Borshchevskii, A.Ya., Trushkov, I.V., and Ioffe, I.I., Fullereny (Fullerens), Moscow Ekzamen., 2005.

    Google Scholar 

  6. Mironov, A.F. Macroheterocycles, 2011, vol. 4, no. 3, p. 186.

    Article  CAS  Google Scholar 

  7. Tzirakis, M.D. and Orfanopoulos, M., Chem. Rev., 2013, vol. 113, no. 7, p. 5262.

    Article  CAS  Google Scholar 

  8. Torre, G., Bottari, G., Sekita, M., Hausmann, A., Guldi, D.M., Orfanopoulous, M., and Torres, T., Chem. Soc. Rev., 2013, vol. 42, no. 20, p. 8049.

    Article  Google Scholar 

  9. Yang, H.-T., Ruan, X.-J., Miao, C.-B., and Sun, X.-Q., Tetrahedron Lett., 2010, vol. 51, p. 6056.

    Article  CAS  Google Scholar 

  10. Yurovskay, M.A. and Trushkov, I.V., Russ. Chem. Bull. Int. Ed., 2002, vol. 51, no. 3, p. 367.

    Article  Google Scholar 

  11. Mateo-Alonso, A., Sooambar, C., and Prato, M., Org. Biomol. Chem., 2006, vol. 4, no. 9, p. 1629.

    Article  CAS  Google Scholar 

  12. Martin, N., Altable, M., Filippone, S., and Martin-Domenech, A., Synlett., 2007, vol. 18, no., 20, p. 3077.

    Article  Google Scholar 

  13. Kharisov, B.I., Kharisova, O.V., Gomez, M.J., and Mendez, U.O., Int. Eng. Chem. Res., 2009, vol. 48, no. 2, p. 545.

    Article  CAS  Google Scholar 

  14. Hirsch, A., Brettreich, M., and Wudl, F., Fullerene: Chemistry and Reactions, Weinhem, Germany Wiley-VCH., 2005.

    Google Scholar 

  15. Fullerenes: Principles and Applications, Landa, F. and Nierengarten, J.-F., Eds., Cambridge RCS Publishing, 2007.

  16. Bourgeois, J.P., Diederich, F., Echegoyen, L., and Nierengarten, J.-F., Helv. Chim. Acta, 1998, vol. 81, no. 10, p. 1835.

    Article  CAS  Google Scholar 

  17. Armaroli, N., Marconi, G., Echegoyen, L., Bourgeois, J.-P., and Diederich, F., Chem. Eur. J., 2000, vol. 6, no. 9, p. 1629.

    Article  CAS  Google Scholar 

  18. Bonifazi, D., Scholl, M., Song, F.I., Echegoyen, L., Accorsi, G., Armaroli, N., and Diederich, F., Angew. Chem. Int. Ed., 2003, vol. 42, no. 40, p. 4966.

    Article  CAS  Google Scholar 

  19. Bonifazi, D., Accorshi, G., Armaroli, N., Song, F.Y., Palkar, A., Echegoyen, L., Scholl, M., Seiler, P., Jaun, B., and Diederich, F., Helv. Chim. Acta, 2005, vol. 88, no. 7, p. 1839.

    Article  CAS  Google Scholar 

  20. Accorsi, G. and Armaroli, N., J. Phys. Chem. C, 2010, vol. 114, no. 3, p. 1385.

    Article  CAS  Google Scholar 

  21. Cheng, P., Wilson, S.R., and Schuster, D.I., Chem. Commun., 1999, no. 1, p. 89.

    Article  Google Scholar 

  22. Wedel, M. and Montforts, F.-P., Tetrahedron Lett., 1999, vol. 40, no. 39, p. 7071.

    Article  CAS  Google Scholar 

  23. Schuster, D.I., Cheng, P., Wilson, S.R., Prokhorenko, V., Katterle, M., Holzwarth, A.R., Braslavsky, S.E., Klihm, G., Williams, R.M., and Luo, C., J. Am. Chem. Soc., 1999, vol. 121, no. 49, p. 11599.

    Article  CAS  Google Scholar 

  24. Guldi, D.M., Luo, C., Prato, M., Dietel, E., and Hirsch, A., Chem. Commun., 2000, no. 5, p. 373.

    Article  Google Scholar 

  25. Guldi, D.M., Luo, C., Da Ros, T., Prato, M., Dietel, E., and Hirsch, A., Chem. Commun., 2000, no. 5, p. 375.

    Article  Google Scholar 

  26. Spänig, F., Kovacs Ch., Hauke, F., Ohkubo, K., Fukuzumi, S., Guldi, D.M., and Hirsch, A., J. Am. Chem. Soc., 2009, vol. 131, no. 23, p. 8180.

    Article  Google Scholar 

  27. Guldi, D.M., Hirsch, A., Scheloske, M., Dietel, E., Troisi, A., Zerbetto, F., and Prato, M., Chem. Eur. J., 2003, vol. 9, no., 20, p. 4968.

    Article  CAS  Google Scholar 

  28. Dietel, E., Hirsch, A., Zhou, J., and Rieker, A., J. Chem. Soc. Perkin. Trans. 2, 1998, no. 6, p. 1357.

    Article  Google Scholar 

  29. Camps, X., Dietel, E., Pyo, S., Echegoyen, L., Hackbarth, S., and Roder, B., Chem. Eur. J., 1999, vol. 5, no. 8, p. 2362.

    Article  CAS  Google Scholar 

  30. Tamaki, K., Imahori, H., Nishimura, Y., Yamazaki, I., Shimomura, A., Okada, T., and Sakata, Y., Chem. Lett., 1999, vol. 28, no. 3, p. 227.

    Article  Google Scholar 

  31. Hasobe, T., Imahori, H., Ohkubo, K., Yamada, H., Sato, T., Nishimura, Yo., Yamazaki, I., and Fukuzumi, Sh., J. Porphyrins Phthalocyanines, 2003, vol. 7, no. 5, p. 296.

    Article  CAS  Google Scholar 

  32. Zheng, G., Dougherty, T.J., and Pandey, R.K., Chem. Commun., 1999, no. 24, p. 2469.

    Article  Google Scholar 

  33. Liddell, P.A., Sumida, J.P., MacPherson, A.N., Noss, L., Seely, G.R., Clark, K.N., Moore, T.A., Moore, A.L., and Gust, D., Photochem. Photobiol., 1994, vol. 60, p. 537.

    Article  CAS  Google Scholar 

  34. Yamada, H., Ohkubo, K., Kuzuhara, D., Takahashi, T., Sandanayaka, A.S.D., Okujima, T., Ohara, K., Ito, O., Uno, H., Ono, N., and Fukuzumi, S., Phys. Chem. B, 2010, vol. 114, no. 45, p. 14717.

    Article  CAS  Google Scholar 

  35. Bell, T.D.M., Ghiggino, K.P., Haynes, A., Langford, S.J., and Woodward, C.P., J. Porphyrins Phthalocyanines, 2007, vol. 11, no. 6, p. 455.

    Article  CAS  Google Scholar 

  36. Krutikova, E.S., Bragina, N.A., and Mironov, A.F., Macroheterocycles, 2011, vol. 4, no. 2, p. 130.

    Article  CAS  Google Scholar 

  37. Zyablikova, E.S., Bragina, N.A., and Mironov, A.F., Mendeleev. Commun., 2012, vol. 22, no. 5, p. 257.

    Article  CAS  Google Scholar 

  38. Krutikova, E.S., Novikov, N.V., Fedulova, I.N., Bragina, N.A., Bykova, N.V., Usol’tseva, V.V., and Anan’eva, G.A., Abstracts of Papers, VIII School and Conference of Young Scientists of Former Soviet Union Countries on the Chemistry of Porphyrins and Related Compounds, Gagra, 2009, p. 29.

    Google Scholar 

  39. Krutikova, E.S., Novikov, N.V., Bragina, N.A., Anan’eva, G.A., Bykova, N.V., and Usol’tseva, V.V., Abstracts of Papers,–III International Scientific and Technical Conference “Science-Rich Chemical Technologies,” Suzdal, 2010, p. 216.

    Google Scholar 

  40. Krutikova, E.S., Bragina, N.A., and Mironov, A.F., Abstracts of Papers, II International Youth School and Conference on the Physical Chemistry of Crown Compounds, Porphyrins, and Phthalocyanines, Tuapse, 2010, p. 56.

    Google Scholar 

  41. Gould, S.L., Kodis, G., Liddell, P.A., Palacios, R.E., Brune, A., Gust, D., Moore, T.A., and Moore, A.L., Tetrahedron, 2006, vol. 62, no. 9, p. 2074.

    Article  CAS  Google Scholar 

  42. Garg, V., Kodis, G., Chachisvilis, M., Hambourger, M., Moore, A.L., Moore, T.A., and Gust, D., J. Am. Chem. Soc., 2011, vol. 133, no. 9, p. 2944.

    Article  CAS  Google Scholar 

  43. Lembo, A., Tagliatesta, P., Cicero, D., Leoni, A., and Salvatori, A., Org. Biomol. Chem., 2009, vol. 7, no. 6, p. 1093.

    Article  CAS  Google Scholar 

  44. Hizume, Y., Tashiro, K., Charvet, R., Yamamoto, Y., Saeki, A., Seki, S., and Aida, T., J. Am. Chem. Soc., 2010, vol. 132, no. 19, p. 6628.

    Article  CAS  Google Scholar 

  45. Molina-Ontoria, A., Wielopolski, M., Gebhardt, J., Gouloumis, A., Clark, T., Guldi, D.M., and Martin, N., J. Am. Chem. Soc., 2011, vol. 133, no. 8, p. 2370.

    Article  CAS  Google Scholar 

  46. Kobori, Y., Shibano, Y., Endo, T. Tsuji, H., Murai, H., and Tamao, K., J. Am. Chem. Soc., 2009, vol. 131, no. 5, p. 1624.

    Article  CAS  Google Scholar 

  47. Nierengarten, J.-Fr., J. Porphyrins Phthalocyanines, 2008, vol. 12, no. 9, p. 1022.

    Article  CAS  Google Scholar 

  48. Lindsey, J.S. and Wagner, R.W., J. Org. Chem., 1989, vol. 54, no. 4, p. 828.

    Article  CAS  Google Scholar 

  49. Guldi, D.M., Chem. Soc. Rev., 2002, vol. 31, no. 1, p. 22.

    Article  CAS  Google Scholar 

  50. Ohkubo, K., Kotani, H., Shao, J., Ou, Z., Kadish, K.M., Li, G., Pandey, R.K., Fujitsuka, M., Ito, O., Imahori, H., and Fukuzumi, S., Angew. Chem. Int. Ed., 2004, vol. 43, no. 7, p. 853.

    Article  CAS  Google Scholar 

  51. Ohkubo, K., Abstracts of Papers, 5th International Conference on Porphyrins and Phtalocyanines (ICPP-5), Moscow, 2008, pp. 45.

    Google Scholar 

  52. Imahori, H., Hagiwara, K., Akiyama, T., Taniguchi, S., Okada, T., and Sakata, Y., Chem. Lett., 1995, vol. 24, no. 4. p. 265-266.

    Article  Google Scholar 

  53. Imahori, H., Hagiwara, K., Masanori, A., Akiyama, T., Taniguchi, S., Okada, T., Shirakawa, M., Sakata, Y., J. Am. Chem. Soc., 1996, vol. 118, no. 47, p. 11771.

    Article  CAS  Google Scholar 

  54. Yamada, K., Imahori, H., Nishimura, Y., Yamazaki, I., and Sakata, Y., Chem. Lett., 1999, vol. 28, no. 9, p. 895.

    Article  Google Scholar 

  55. Imahori, H., El-Khouly, M.E., Fujitsuka, M., Ito, O., Sakata, Y., and Fukuzumi, S., J. Phys. Chem., A, 2001, vol. 105, no. 2, p. 325.

    Article  CAS  Google Scholar 

  56. Fong II, R., Schuster, D.I., and Wilson, S.R., Org. Lett., 1999, vol. 1, no. 5, p. 729.

    Article  Google Scholar 

  57. Wielopolski, M., G. de Miguel Rojas, C. van der Pol Brinkhaus, L., Katsukis G, Bryce, M.R., Clark, T., and Guldi, D.M., ACS Nano, 2010, vol. 4, no. 11, p. 6449.

    Article  CAS  Google Scholar 

  58. Ranasinghe, M.G., Oliver, A.M., Rothenfluh, D.F., Salek, A., and Paddon-Row, M.N., Tetrahedron Lett., 1996, vol. 37, no. 27, p. 4797.

    Article  CAS  Google Scholar 

  59. Bell, T.D.M., Smith, T.A., Ghiggino, K.P., Ranasinghe, M.G., Shephard, M.J., and Raddon-Row, M.N., Chem. Phys. Lett., 1997, vol. 268, nos. 3–4, p. 223.

    Article  CAS  Google Scholar 

  60. Baran, P.S., Monaco, R.R., Khan, A.U., Schuster, D.I., and Wilson, S.R., J. Am. Chem. Soc., 1997, vol. 119, no. 35, p. 8363.

    Article  CAS  Google Scholar 

  61. Safonov, I.G., Baran, P.S., and Schuster, D.I., Tetrahedron Lett., 1997, vol. 38, no. 47, p. 8133.

    Article  CAS  Google Scholar 

  62. Kawaguchi, M., Ikeda, A., Hamachi, I., and Shinkai, S., Tetrahedron Lett., 1999, vol. 40, no. 47, p. 8245.

    Article  CAS  Google Scholar 

  63. Megiatto, J.D., Schuster, D.I., Abwandner, S., Miguel, G., and Guldi, D.M., J. Am. Chem. Soc., 2010, vol. 132, no. 11, p. 3847.

    Article  CAS  Google Scholar 

  64. Jung, S., Seo, J., and Shin, S.K., J. Phys. Chem., A, 2010, vol. 114, no. 43, p. 11376.

    Article  CAS  Google Scholar 

  65. Poddutoori, P.K., Sandanayaka, A.S.D., and Hasobe, T., J. Phys. Chem. B, 2010, vol. 114, no. 45, p. 14348.

    Article  CAS  Google Scholar 

  66. Da Ros, T., Prato, M., Guildi, D.M., Alessio, E., Ruzzi, M., and Pasimeni, L., Chem Commun., 1999, no. 7, p. 635.

    Article  Google Scholar 

  67. Da Ros, T., Prato, M., Guildi, D.M., Ruzzi, A., and Pasimeni, L., Chem. Eur. J., 2001, vol. 7, no. 4, p. 816.

    Article  Google Scholar 

  68. D’Souza, F., Rath, N.P., Deviprasad, G.R., and Zandler, V.T., Chem. Commun., 2001, no. 3, p. 267.

    Article  Google Scholar 

  69. Armaroli, N., Diederich, F., Echengoyen L., Habicher, T., Flamigni, L., Marconi, G., and Nierengarten, J.-F., New J. Chem., 1999, no. 1, p. 77.

    Article  Google Scholar 

  70. D’Souza, F., Deviprasad, G.R., Rahman, M.S., and Choi, J.-P., Inorg. Chem., 1999, vol.38, no. 9, p. 2157.

    Article  Google Scholar 

  71. D’Souza, F., Deviprasad, G.R., El-Khouly, M.E., Fujitsuka, M., and Ito, O. J. Am. Chem. Soc., 2001, vol. 123, no. 22, p. 5277.

    Article  Google Scholar 

  72. Santos, L.G., Carvalho Da-Silva, D., Reboucas, J.S., Alves, M.R.A., Idemori, Y.M., Matencio, T., Freitas, R.P., and Alves, R.B., Tetrahedron, 2011, vol. 67, no. 1, p. 228.

    Article  CAS  Google Scholar 

  73. Kawashima, Y., Ohkubo, K., Kentaro, M., and Fukuzumi, Sh., Phys. Chem., C, 2013, vol. 117, p. 21166.

    Article  CAS  Google Scholar 

  74. Al-Subi, A.H., Niemi, M., Tkachenko, N.V., and Lemmetyinen, H., Phys. Chem., A, 2011, vol. 115, no. 41, p. 3263.

    Article  CAS  Google Scholar 

  75. Song, J., Aratani, N., Shinokubo, H., and Osuka, A., J. Am. Chem. Soc., 2010, vol. 132, no. 46, p. 16356.

    Article  CAS  Google Scholar 

  76. Tkachenko, N.V., Vehmanen, V., Efimov, A., and Lemmetyinen, H., J. Porphyrins Phthalocyanines, 2003, vol. 7, nos. 4–5, p. 255.

    Article  CAS  Google Scholar 

  77. Wolffs, M., Hoeben, F.J.M., Beckers, E.H.A., Schenning, A.P.H.J., and Meijer, E.W., J. Am. Chem. Soc., 2005, vol. 127, no. 39, p. 13484.

    Article  CAS  Google Scholar 

  78. Hosseini, A., Hodgson, M.C., Tham, F.S., Reed, C.A., and Boyd, P., Cryst. Growth Des., 2006, vol. 6, no. 2, p. 397.

    Article  CAS  Google Scholar 

  79. Nobukuni, H., Tani, F., Shimazaki, Y., Naruta, Y., Ohkubo, K., Nakanishi, T., Kojima, T., Fukuzumi, Sh., and Seki, Sh., J. Phys. Chem., C, 2009, vol. 113, no. 45, p. 19694.

    Article  CAS  Google Scholar 

  80. Sakaguchi, K., Kamimura, T., Uno, H., Mori, S., Ozako, S., Nobukuni, H., Ishida, M., and Tani, F., J. Org. Chem., 2014, vol. 79, no. 7, p. 2980.

    Article  CAS  Google Scholar 

  81. Gil-Ramirez, G., Karlen, S.D., Shundo, A., Porfyrakis, K., Ito, Y., Briggs, G.A.D., Morton, J.J.L., and Anderson, H.L., Org. Lett., 2010, vol. 12, no. 15, p. 3544.

    Article  CAS  Google Scholar 

  82. Kharisov, B. I., Kharisova, O.V., Gomez, M.J., and Mendez, U.O., Ind. Eng. Chem. Res., 2009, vol. 48, no. 2, p. 545.

    Article  CAS  Google Scholar 

  83. Khana, T.K, Bröringb, M., Mathura, S., and Ravikanthc, M., Coord. Chem. Rev., 2013, vol. 257, nos. 15–16, p. 2348.

    Article  Google Scholar 

  84. Razumov, V.F., Efimov, O.N., Kaplunov, M.T., Klyuev, M.V., Klyueva, M.E., Lomova, T.I., Tarasov, B.P., Troshin, P.A., and Yarmolenko, O.V., in Nanostrukturirovannye materialy dlya sistem zapasaniya i preobrazovaniya energii (Nanostructured Materials for Energy Storage and Conversion Systems), Razumov, V.F. and Klyuev, M.V., Eds., Ivanovo Ivanov. Gos. Univ., 2007.

  85. Valentin, M.D., Bisol, A., Agostini, G., Fuhs, M., Liddell, P.A., Moore, A.L., Moore, T.A., Gust, D., and Carbonera, D., J. Am. Chem. Soc., 2004, vol. 126, no. 51, p. 17074.

    Article  Google Scholar 

  86. Imahori, H. K. Y., Kashiwagi, Y., Hasobe, T., Kimura, M., Hanada, T., Nishimura, Y., Yamazaki, I., Araki, Y., Ito, O., and Fukuzumi, S., Thin Solid Films, 2004, no. 451, p. 580.

    Article  Google Scholar 

  87. Imahori, H., Mori, Y., and Matano, Y., J. Photochem. Photobiol., C, 2003, vol. 4, no. 1, p. 51.

    Article  CAS  Google Scholar 

  88. Amirshahi, N., Alyautdin, R.N., Rezayat, S.M., Sarkar, S., Orlova, M.A., Orlov, P.A., Poloznikov, A.A., and Kuznetsov, D.A., Chromatographia, 2008, vol. 68, nos. 3–4, p. 295.

    Article  CAS  Google Scholar 

  89. Umeyama, T.I.H. and Imahori, H., Photosynthesis Research., 2006, vol. 87, no. 1, p. 63.

    Article  CAS  Google Scholar 

  90. Wakahara, T., D’Angelo, P., Miyazawa, K., Nemoto, Y., Ito, O., Tanigaki, N., Bradley, D.D.C., and Anthopoulos, T.D., J. Am. Chem. Soc., 2012, vol. 134, no. 17, p. 7204.

    Article  CAS  Google Scholar 

  91. Nawaz, M. H., Xu, L., Liu, F., and Zhang, W., RSC Adv., 2013, vol. 3, no. 24, p. 9206.

    Article  CAS  Google Scholar 

  92. Zhao, H., Chen, C., Zhu, Y., Shi, M., and Zheng, J., J. Nanopart Res., 2012, vol. 14, no. 3, p. 765.

    Article  Google Scholar 

  93. Velez, J.P., Aguirre, M.J., Cattin, L., Makha, M., and Bernede, J.C., J. Porphyrins Phthalocyanines, 2014, vol. 18, no. 5, p. 347.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to F. M. Karmova.

Additional information

Original Russian Text © F.M. Karmova, V.S. Lebedeva, A.F. Mironov, 2014, published in Rossiiskii Khimicheskii Zhurnal, 2014, Vol. 58, Nos. 5–6, pp. 3–29.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karmova, F.M., Lebedeva, V.S. & Mironov, A.F. Fullerene-containing porphyrins: Synthesis and potential practical applications. Russ J Gen Chem 86, 2145–2179 (2016). https://doi.org/10.1134/S1070363216090322

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363216090322

Navigation