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.
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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.
Yushkin, N.P., Dokl. Akad. Nauk, 1994, vol. 337, no. 6, p. 800.
Reznikov, V.A. and Polehovskii, Yu.S., Pis’ma v Zh. Tekh. Fiz., 2000, vol. 26, no. 15, p. 94.
Buseck, P.R., Earth Planet. Sci. Lett., 2002, vol. 203, no. 4. p. 781.
Sidorov, L.N., Yurovskaya, M.A., Borshchevskii, A.Ya., Trushkov, I.V., and Ioffe, I.I., Fullereny (Fullerens), Moscow Ekzamen., 2005.
Mironov, A.F. Macroheterocycles, 2011, vol. 4, no. 3, p. 186.
Tzirakis, M.D. and Orfanopoulos, M., Chem. Rev., 2013, vol. 113, no. 7, p. 5262.
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.
Yang, H.-T., Ruan, X.-J., Miao, C.-B., and Sun, X.-Q., Tetrahedron Lett., 2010, vol. 51, p. 6056.
Yurovskay, M.A. and Trushkov, I.V., Russ. Chem. Bull. Int. Ed., 2002, vol. 51, no. 3, p. 367.
Mateo-Alonso, A., Sooambar, C., and Prato, M., Org. Biomol. Chem., 2006, vol. 4, no. 9, p. 1629.
Martin, N., Altable, M., Filippone, S., and Martin-Domenech, A., Synlett., 2007, vol. 18, no., 20, p. 3077.
Kharisov, B.I., Kharisova, O.V., Gomez, M.J., and Mendez, U.O., Int. Eng. Chem. Res., 2009, vol. 48, no. 2, p. 545.
Hirsch, A., Brettreich, M., and Wudl, F., Fullerene: Chemistry and Reactions, Weinhem, Germany Wiley-VCH., 2005.
Fullerenes: Principles and Applications, Landa, F. and Nierengarten, J.-F., Eds., Cambridge RCS Publishing, 2007.
Bourgeois, J.P., Diederich, F., Echegoyen, L., and Nierengarten, J.-F., Helv. Chim. Acta, 1998, vol. 81, no. 10, p. 1835.
Armaroli, N., Marconi, G., Echegoyen, L., Bourgeois, J.-P., and Diederich, F., Chem. Eur. J., 2000, vol. 6, no. 9, p. 1629.
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.
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.
Accorsi, G. and Armaroli, N., J. Phys. Chem. C, 2010, vol. 114, no. 3, p. 1385.
Cheng, P., Wilson, S.R., and Schuster, D.I., Chem. Commun., 1999, no. 1, p. 89.
Wedel, M. and Montforts, F.-P., Tetrahedron Lett., 1999, vol. 40, no. 39, p. 7071.
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.
Guldi, D.M., Luo, C., Prato, M., Dietel, E., and Hirsch, A., Chem. Commun., 2000, no. 5, p. 373.
Guldi, D.M., Luo, C., Da Ros, T., Prato, M., Dietel, E., and Hirsch, A., Chem. Commun., 2000, no. 5, p. 375.
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.
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.
Dietel, E., Hirsch, A., Zhou, J., and Rieker, A., J. Chem. Soc. Perkin. Trans. 2, 1998, no. 6, p. 1357.
Camps, X., Dietel, E., Pyo, S., Echegoyen, L., Hackbarth, S., and Roder, B., Chem. Eur. J., 1999, vol. 5, no. 8, p. 2362.
Tamaki, K., Imahori, H., Nishimura, Y., Yamazaki, I., Shimomura, A., Okada, T., and Sakata, Y., Chem. Lett., 1999, vol. 28, no. 3, p. 227.
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.
Zheng, G., Dougherty, T.J., and Pandey, R.K., Chem. Commun., 1999, no. 24, p. 2469.
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.
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.
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.
Krutikova, E.S., Bragina, N.A., and Mironov, A.F., Macroheterocycles, 2011, vol. 4, no. 2, p. 130.
Zyablikova, E.S., Bragina, N.A., and Mironov, A.F., Mendeleev. Commun., 2012, vol. 22, no. 5, p. 257.
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.
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.
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.
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.
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.
Lembo, A., Tagliatesta, P., Cicero, D., Leoni, A., and Salvatori, A., Org. Biomol. Chem., 2009, vol. 7, no. 6, p. 1093.
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.
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.
Kobori, Y., Shibano, Y., Endo, T. Tsuji, H., Murai, H., and Tamao, K., J. Am. Chem. Soc., 2009, vol. 131, no. 5, p. 1624.
Nierengarten, J.-Fr., J. Porphyrins Phthalocyanines, 2008, vol. 12, no. 9, p. 1022.
Lindsey, J.S. and Wagner, R.W., J. Org. Chem., 1989, vol. 54, no. 4, p. 828.
Guldi, D.M., Chem. Soc. Rev., 2002, vol. 31, no. 1, p. 22.
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.
Ohkubo, K., Abstracts of Papers, 5th International Conference on Porphyrins and Phtalocyanines (ICPP-5), Moscow, 2008, pp. 45.
Imahori, H., Hagiwara, K., Akiyama, T., Taniguchi, S., Okada, T., and Sakata, Y., Chem. Lett., 1995, vol. 24, no. 4. p. 265-266.
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.
Yamada, K., Imahori, H., Nishimura, Y., Yamazaki, I., and Sakata, Y., Chem. Lett., 1999, vol. 28, no. 9, p. 895.
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.
Fong II, R., Schuster, D.I., and Wilson, S.R., Org. Lett., 1999, vol. 1, no. 5, p. 729.
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.
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.
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.
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.
Safonov, I.G., Baran, P.S., and Schuster, D.I., Tetrahedron Lett., 1997, vol. 38, no. 47, p. 8133.
Kawaguchi, M., Ikeda, A., Hamachi, I., and Shinkai, S., Tetrahedron Lett., 1999, vol. 40, no. 47, p. 8245.
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.
Jung, S., Seo, J., and Shin, S.K., J. Phys. Chem., A, 2010, vol. 114, no. 43, p. 11376.
Poddutoori, P.K., Sandanayaka, A.S.D., and Hasobe, T., J. Phys. Chem. B, 2010, vol. 114, no. 45, p. 14348.
Da Ros, T., Prato, M., Guildi, D.M., Alessio, E., Ruzzi, M., and Pasimeni, L., Chem Commun., 1999, no. 7, p. 635.
Da Ros, T., Prato, M., Guildi, D.M., Ruzzi, A., and Pasimeni, L., Chem. Eur. J., 2001, vol. 7, no. 4, p. 816.
D’Souza, F., Rath, N.P., Deviprasad, G.R., and Zandler, V.T., Chem. Commun., 2001, no. 3, p. 267.
Armaroli, N., Diederich, F., Echengoyen L., Habicher, T., Flamigni, L., Marconi, G., and Nierengarten, J.-F., New J. Chem., 1999, no. 1, p. 77.
D’Souza, F., Deviprasad, G.R., Rahman, M.S., and Choi, J.-P., Inorg. Chem., 1999, vol.38, no. 9, p. 2157.
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.
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.
Kawashima, Y., Ohkubo, K., Kentaro, M., and Fukuzumi, Sh., Phys. Chem., C, 2013, vol. 117, p. 21166.
Al-Subi, A.H., Niemi, M., Tkachenko, N.V., and Lemmetyinen, H., Phys. Chem., A, 2011, vol. 115, no. 41, p. 3263.
Song, J., Aratani, N., Shinokubo, H., and Osuka, A., J. Am. Chem. Soc., 2010, vol. 132, no. 46, p. 16356.
Tkachenko, N.V., Vehmanen, V., Efimov, A., and Lemmetyinen, H., J. Porphyrins Phthalocyanines, 2003, vol. 7, nos. 4–5, p. 255.
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.
Hosseini, A., Hodgson, M.C., Tham, F.S., Reed, C.A., and Boyd, P., Cryst. Growth Des., 2006, vol. 6, no. 2, p. 397.
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.
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.
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.
Kharisov, B. I., Kharisova, O.V., Gomez, M.J., and Mendez, U.O., Ind. Eng. Chem. Res., 2009, vol. 48, no. 2, p. 545.
Khana, T.K, Bröringb, M., Mathura, S., and Ravikanthc, M., Coord. Chem. Rev., 2013, vol. 257, nos. 15–16, p. 2348.
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.
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.
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.
Imahori, H., Mori, Y., and Matano, Y., J. Photochem. Photobiol., C, 2003, vol. 4, no. 1, p. 51.
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.
Umeyama, T.I.H. and Imahori, H., Photosynthesis Research., 2006, vol. 87, no. 1, p. 63.
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.
Nawaz, M. H., Xu, L., Liu, F., and Zhang, W., RSC Adv., 2013, vol. 3, no. 24, p. 9206.
Zhao, H., Chen, C., Zhu, Y., Shi, M., and Zheng, J., J. Nanopart Res., 2012, vol. 14, no. 3, p. 765.
Velez, J.P., Aguirre, M.J., Cattin, L., Makha, M., and Bernede, J.C., J. Porphyrins Phthalocyanines, 2014, vol. 18, no. 5, p. 347.
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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.
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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
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DOI: https://doi.org/10.1134/S1070363216090322