Structure and Electrochemical Property of Fullerene Dimers

doi:10.6023/cjoc201605022

Abstract

Fullerene dimers have attracted extensive attention due to their unique structures and fascinating properties. Hundreds of fullerene dimers have been isolated so far, including the singly-bonded fullerene dimers, fullerene dimers connected by electroactive bridges, all-carbon fullerene dimers and unsymmetrical dimers, etc. These new molecular systems have potential applications in the area of artificial photosynthesis, photoelectronic device and supramolecular chemistry. Based on the different structure types, various fullerene dimers reported are summarized and classified in this review. Furthermore, the electrochemistry property of the dimers is discussed and the research trend of this area is also prospected.

Key words: fullerene, dimer, electrochemistry

Cite this article

Chang Weiwei, Zhao Zengdian. Structure and Electrochemical Property of Fullerene Dimers[J]. Chin. J. Org. Chem., 2016, 36(11): 2651-2661.

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References

[1] Kratschmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Nature 1990, 347, 354.
[2] Sánchez, L.; Sierra, M.; Martín, N.; Guldi, D. M.; Wienk, M. W.; Janssen, R. A. J. Org. Lett. 2005, 7, 1691.
[3] (a) Martin, C. A.; Ding, D.; Sørensen, J. K.; Bjørnholm, T.; van Ruitenbeek, J. M.; van der Zant, H. S. J. J. Am. Chem. Soc. 2008, 130, 13198.
(b) Wang T. T.; Zeng, H, P. Chin. J. Org. Chem. 2008, 28, 1303 (in Chinese). (王婷婷, 曾和平, 有机化学, 2008, 28, 1303.)
[4] (a) Delgado, J. L.; Espíldora, E.; Liedtke, M.; Sperlich, A.; Rauh, D.; Baumann, A.; Deibel, C.; Dyakonov, V.; Martín, N. Chem.-Eur. J. 2009, 15, 13474.
(b) Liu, J.; Guo, X.; Qin, Y.; Liang, S.; Guo, Z.-X.; Li, Y. J. Mater. Chem. 2012, 22, 1758.
(c) Morinaka, Y.; Nobori, M.; Murata, M.; Wakamiya, A.; Sagawa, T.; Susumu, Y.; Murata, Y. Chem. Commun. 2013, 49, 3670.
(d) Guo, Y.; Zhu, H.; Liu, G.; Yan, H.; Zhu, B.; Li, S.; Sun, Y.; Li, G. J. Org. Chem. 2016, 36, 172 (in Chinese). (郭颖, 朱华新, 刘桂林, 严慧敏, 朱冰洁, 李帅, 孙亚军, 李果华, 有机化学, 2016, 36, 172.)
[5] (a) Segura, J. L.; Martin, N. Chem. Soc. Rev. 2000, 29, 13.
(b) Giacalone, F.; Martín, N. Chem. Rev. 2006, 106, 5136.
(c) Wei, X.; Luo, W.; Wei, X. W. Chin. J. Org. Chem. 2007, 27, 153 (in Chinese). (魏祥龙, 罗薇, 魏先文, 有机化学, 2007, 27, 153.)
[6] Komatsu, K. In Organic Solid State Reactions, Ed.:Toda, F., Springer Berlin Heidelberg, Berlin, Heidelberg, 2005, pp. 185~206.
[7] Kellner, I. D.; von Gernler, M. S.; Tzirakis, M. D.; Orfanopoulos, M.; Drewello, T. J. Phys. Chem. C 2014, 118, 30253.
[8] Yoshida, M.; Sultana, F.; Uchiyama, N.; Yamada, T.; Iyoda, M. Tetrahedron Lett. 1999, 40, 735.
[9] Nambo, M.; Wakamiya, A.; Yamaguchi, S.; Itami, K. J. Am. Chem. Soc. 2009, 131, 15112.
[10] Nambo, M.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2011, 133, 2402.
[11] Itami, K. Chem. Rec. 2011, 11, 226.
[12] Nambo, M.; Itami, K. Chem.-Eur. J. 2009, 15, 4760.
[13] Lu, S.; Jin, T.; Kwon, E.; Bao, M.; Yamamoto, Y. Angew. Chem., Int. Ed. 2012, 51, 802.
[14] Lu, S.; Jin, T.; Bao, M.; Yamamoto, Y. Org. Lett. 2012, 14, 3466.
[15] Zhang, T.-H.; Lu, P.; Wang, F.; Wang, G.-W. Org. Biomol. Chem. 2003, 1, 4403.
[16] Wang,G.-W.; Wang,C.-Z.; Zhu, S.-E.; Murata, Y. Chem. Cummun. 2011, 47, 6111.
[17] Cheng, F.; Murata, Y.; Komatsu, K. Org. Lett. 2002, 4, 2541.
[18] Yang, W.-W.; Li, Z.-J.; Gao, X. J. Org. Chem. 2011, 76, 6067.
[19] Smith, A. B.; Tokuyama, H.; Strongin, R. M.; Furst, G. T.; Romanow, W. J.; Chait, B. T.; Mirza, U. A.; Haller, I. J. Am. Chem. Soc. 1995, 117, 9359.
[20] Lebedkin, S.; Ballenweg, S.; Gross, J.; Taylor, R.; Krätschmer, W. Tetrahedron Lett. 1995, 36, 4971.
[21] Taylor, R.; Barrow, M. P.; Drewello, T. Chem. Commun. 1998, 2497.
[22] Balch, A. L.; Costa, D. A.; Fawcett, W. R.; Winkler, K. J. Phys. Chem. 1996, 100, 4823.
[23] Gromov, A.; Lebedkin, S.; Ballenweg, S.; G. Avent, A.; Taylor, R.; Kratschmer, W. Chem. Commun. 1997, 209.
[24] Tsyboulski, D.; Heymann, D.; Bachilo, S. M.; Alemany, L. B.; Weisman, R. B. J. Am. Chem. Soc. 2004, 126, 7350.
[25] Giesa, S.; H. Gross, J.; Gleiter, R.; Giesa, S.; Gromov, A.; Kratschmer, W.; E. Hull, W.; Lebedkin, S. Chem. Commun. 1999, 465.
[26] Dragoe, N.; Shimotani, H.; Hayashi, M.; Saigo, K.; de Bettencourt-Dias, A.; Balch, A. L.; Miyake, Y.; Achiba, Y.; Kitazawa, K. J. Org. Chem. 2000, 65, 3269.
[27] Murata, Y.; Kato, N.; Komatsu, K. J. Org. Chem. 2001, 66, 7235.
[28] Fujiwara, K.; Komatsu, K. Org. Lett. 2002, 4, 1039.
[29] Murata, Y.; Han, A.; Komatsu, K. Tetrahedron Lett. 2003, 44, 8199.
[30] Wang, G.-W.; Komatsu, K.; Murata, Y.; Shiro, M. Nature 1997, 387, 583.
[31] Komatsu, K.; Wang, G.-W.; Murata, Y.; Tanaka, T.; Fujiwara, K.; Yamamoto, K.; Saunders, M. J. Org. Chem. 1998, 63, 9358.
[32] Makarova, T. L. Semiconductors 2011, 35, 243.
[33] Pusztai, T.; Faigel, G.; Gránásy, L.; Tegze, M.; Pekker, S. Europhys. Lett. 1995, 32, 721.
[34] (a) Lee, K. H.; Park, S. S.; Suh, Y.; Yamabe, T.; Osawa, E.; Lüthi, H. P.; Gutta, P.; Lee, C. J. Am. Chem. Soc. 2001, 123, 110856.
(b) Zhang, G. Chin. J. Org. Chem 2012, 32, 1010 (in Chinese). (张改红, 有机化学, 2012, 32, 1010.)
[35] Komatsu, K.; Fujiwara, K.; Tanaka, T.; Murata, Y. Carbon 2000, 38, 1529.
[36] Dragoe, N.; Shimotani, H.; Wang, J.; Iwaya, M.; de Bettencourt-Dias, A.; Balch, A. L.; Kitazawa, K. J. Am. Chem. Soc. 2001, 123, 1294.
[37] Ren, T.; Sun, B.; Chen, Z.; Qu, L.; Yuan, H.; Gao, X.; Wang, S.; He, R.; Zhao, F.; Zhao, Y.; Liu, Z.; Jing, X. J. Phys. Chem. B 2007, 111, 6344.
[38] Zhao, Y.; Chen, Z.; Yuan, H.; Gao, X.; Qu, L.; Chai, Z.; Xing, G.; Yoshimoto, S.; Tsutsumi, E.; Itaya, K. J. Am. Chem. Soc. 2004, 126, 11134.
[39] Anderson, H. L.; Faust, R.; Rubin, Y.; Diederich, F. Angew. Chem., In. Ed 1994, 33, 1366.
[40] Timmerman, P.; Witschel, L. E.; Diederich, F.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M. Helv. Chim. Acta 1996, 79, 6.
[41] Komatsu, K.; Takimoto, N.; Murata, Y.; Wan, T. S. M.; Wong, T. Tetrahedron Lett. 1996, 37, 6153.
[42] Paquette, L. A.; Graham, R. J., J. Org. Chem. 1995, 60, 2958.
[43] (a) Wang, G.-W.; Chen, Z.-X.; Murata, Y.; Komatsu, K. Tetrahedron 2005, 61, 4851.
(b) Zhu, Y.-L.; Zhou, S.-Y.; Cao, L.; Kan, Y.-H. Chin. J. Org. Chem. 2007, 27, 313 (in Chinese). (朱玉兰, 周书雨, 曹丽, 阚玉和, 有机化学, 2007, 27, 313.)
[44] (a) Zhang, J.; Porfyrakis, K.; Morton, J. J.; Sambrook, M. R.; Harmer, J.; Xiao, L.; Ardavan, A.; Briggs, G. A. D. J. Phys. Chem. C 2008, 112, 2802.
(b) Zhang, S.; Gan, L.; Huang, C.; Lu, M.; Pan, J.; He, X. J. Org. Chem. 2002, 67, 883.
[45] Briggs, J. B.; Miller, G. P. C. R. Chim. 2006, 9, 916.
[46] Delgado, J. L.; Osuna, S.; Bouit, P.-A.; Martínez-Alvarez, R.; Espíldora, E.; Solà, M.; Martín, N. J. Org. Chem. 2009, 74, 8174.
[47] (a) Belik, P.; Gügel, A.; Spickermann, J.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 78.
(b) Gügel, A.; Belik, P.; Walter, M.; Kraus, A.; Harth, E.; Wagner, M.; Spickermann, J.; Müllen, K. Tetrahedron 1996, 52, 5007.
(c) Murata, Y.; Kato, N.; Fujiwara, K.; Komatsu, K. J. Org. Chem. 1999, 64, 3483.
(d) de Lucas, A. I.; Martín, N.; Sánchez, L.; Seoane, C. Tetrahedron Lett. 1996, 37, 9391.
(e) Martín, N.; Sánchez, L.; Illescas, B.; Pérez, I. Chem. Rev. 1998, 98, 2527.
(f) Armspach, D.; Constable, E. C.; Diederich, F.; Housecroft, C. E.; Nierengarten, J.-F. Chem.-Eur. J. 1998, 4, 723.
(g) Konev, A. S.; Khlebnikov, A. F.; Frauendorf, H. J. Org. Chem. 2011, 76, 6218.
[48] Xiao, Z.; Matsuo, Y.; Maruyama, M.; Nakamura, E. Org. Lett. 2013, 15, 2176.
[49] Chang, W.-W.; Li, Z.-J.; Gao, X. Org. Lett. 2013, 15, 1642.
[50] Li, Z.-J.; Li, S.-H.; Sun, T.; Gao, X. J. Org. Chem. 2014, 79, 197.
[51] Li, Z.-J.; Li, S.-H.; Sun, T.; Hou, H.-L.; Gao, X. J. Org. Chem. 2015, 80, 3566.
[52] (a) Konarev, D. V.; Troyanov, S. I.; Nakano, Y.; Ustimenko, K. A.; Otsuka, A.; Yamochi, H.; Saito, G.; Lyubovskaya, R. N. Organometallics 2013, 32, 4038.
(b) Lee, K.; Song, H.; Kim, B.; Park, J. T.; Park, S.; Choi, M. -G. J. Am. Chem. Soc. 2002, 124, 2872.
[53] Park, B. K.; Lee, G.; Kim, K. H.; Kang, H.; Lee, C. Y.; Miah, M. A.; Jung, J.; Han, Y.-K.; Park, J. T. J. Am. Chem. Soc. 2006, 128, 11160.
[54] Nakamura, E.; Mouri, S.; Nakamura, Y.; Harano, K.; Isobe, H. Org. Lett. 2008, 10, 4923.
[55] Fujiwara, K.; Komatsu, K.; Wang, G.-W.; Tanaka, T.; Hirata, K.; Yamamoto, K.; Saunders, M. J. Am. Chem. Soc. 2001, 123, 10715.

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