Abstract
The reduction of fullerene C60 by Zn and Mg in DMF was studied both in the presence and absence of KOH. Fullerene C60 was reduced in these systems to form the C60 n– (n = 1, 2, and 3) anions. The anions were detected by optical and ESR spectroscopies. It was found that Mg reduced C60 to the monoanion, Mg/KOH and Zn reduced C60 to the dianion, and Zn/KOH reduced C60 to the trianion. Like KCN, potassium hydroxide adds to fullerene upon interaction with C60 in DMF. The reaction of C60 with KOH in benzonitrile was accompanied by the generation of the fullerene monoanion. A possible mechanism of the formation of fullerene monoanions in the presence of KOH is discussed. The degradation of the C60 n– anions in air was studied.
Similar content being viewed by others
References
C. Bossara, S. Rigaut, D. Astruc, M. H. Delville, G. Felix, A. Fevrier-Bouveir, J. Amiell, S. Flandrois, and P. Delxaes, J. Chem. Soc., Chem. Commun., 1993, 333.
P. Bhyrappa, P. Paul, J. Stinchcombe, P. D. W. Boyd, and C. A. Reed, J. Am. Chem. Soc., 1993, 115, 11004.
C. Boulas, R. Subramanian, W. Kutner, M. T. Jones, and K. M. Kadish, J. Electrochem. Soc., 1993, 140, L130.
A. S. Lobach, N. F. Goldshleger, M. G. Kaplunov, and A. V. Kulikov, Chem. Phys. Lett., 1995, 24, 322.
S. P. Solodovnikov, Izv. Akad. Nauk, Ser. Khim., 1996, 2256 [Russ. Chem. Bull., 1996, 45, 2141 (Engl. Transl.)].
M. J. Rosseinsky, J. Mater. Chem., 1995, 5, 1497.
P. W. Stephens, D. Cox, J. W. Lauher, L. Mihaly, J. B. Wiley, P.-M. Allemand, A. Hirsch, K. Holczer, Q. Li, J. D. Thompson, and F. Wudl, Nature (London), 1992, 355, 331.
D. V. Konarev and R. N. Lyubovskaya, Usp. Khim., 1999, 68, 23 [Russ. Chem. Rev., 1999, 68 (Engl. Transl.)].
D. Dubois and K. M. Kadish, J. Am. Chem. Soc., 1991, 113, 4364.
M. Khaled, R. T. Carlin, P. C. Trulove, G. R. Eaton, and S. S. Eaton, J. Am. Chem. Soc., 1994, 116, 3465.
D. Dubois, M. T. Jones, and K. M. Kadish, J. Am. Chem. Soc., 1992, 114, 6446.
D. V. Konarev, N. V. Drichko, and A. Graja, J. Chim. Phys., 1998, 95, 2143.
M. F. Wu, X. W. Wei, L. Qi, and Z. Xu, Tetrahedron Lett., 1996, 37, 7409.
X. Wei, Z. Suo, K. Zhou, Z. Xu, W. Zhang, R. Wang, H. Shen, and X. Li, J. Chem. Soc., Perkin Trans. 2, 1999, 121.
X. Wei, Z. Suo, K. Yin, and Z. Xu, J. Organomet. Chem., 2000, 599, 69; S. Takekuma, H. Takekuma, T. Matsumoto, and Z. Yoshida, Tetrahedron Lett., 2000, 41, 2929.
R. Sabramanian, P. Boulas, M. N. Vijayashree, F. D´Souza, M. T. Jones, and K. M. Kadish, J. Chem. Soc., Chem. Commun., 1994, 1847.
M. T. Jones, K. M. Kadish, R. Subramanian, P. Boulas, and M. N. Vijayashree, Synth. Met., 1995, 70, 1341.
C. A. Reed and R. D. Bolkskar, Chem. Rev., 2000, 100, 1075.
S. Fukuzumi, I. Nakanishi, J. Maruta, T. Yorisue, T. Suenobu, S. Itoh, R. Arakawa, and K. M. Kadish, J. Am. Chem. Soc., 1998, 120, 6673.
X. Wei, Z. Suo, G. Yin, and Z. Xu, J. Organomet. Chem., 2000, 599, 69.
Ch. K. Mann and K. K. Barnes, Electrochemical Reactions in Nonaqueous Systems, Marcel Dekker Inc., New York, 1970.
D. Dubois, G. Moninot, W. Kurner, M. T. Jones, and K. M. Kadish, J. Phys. Chem., 1992, 96, 7137.
M. Keshavarz, B. Knight, G. Srdanov, and F. Wudl, J. Am. Chem. Soc., 1995, 117, 11371.
M. E. Vol´pin, Z. N. Parnes, and V. S. Romanova, Izv. Akad. Nauk, Ser. Khim., 1998, 1050 [Russ. Chem. Bull., 1998, 47, 1021 (Engl. Transl.)].
E. M. Belavtseva, E. V. Kichenko, V. S. Romanova, Z. N. Parnes, and M. E. Vol´pin, Izv. Akad. Nauk, Ser. Khim., 1996, 876 [Russ. Chem. Bull., 1996, 45, 831 (Engl. Transl.)].
S. R. Wilson and Y. J. Wu, J. Am. Chem. Soc., 1993, 115, 10334.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Litvinov, A.L., Konarev, D.V., Yudanova, E.I. et al. Selective reduction of fullerene C60 by metals in neutral and alkaline media. Interaction of C60 with KOH. Russian Chemical Bulletin 51, 2003–2007 (2002). https://doi.org/10.1023/A:1021695423077
Issue Date:
DOI: https://doi.org/10.1023/A:1021695423077