Abstract
In this study, methanofullerenes and 2′,3′-dihydrofuran C60 derivatives were selectively synthesized in high yields via the reactions of C60 with β-keto esters under mild conditions by controlling the addition sequence and molar ratio of iodine and base. The structures of the products were determined by spectroscopic characterization. Moreover, a possible reaction mechanism for the selective formation of fullerene derivatives was proposed.
Highlights
Fullerenes have attracted signi cant attention from chemists due to their unique geometric and electronic structures.[1,2,3] To date, the functionalization of fullerenes is of great importance for fullerene chemistry since fullerenes can be synthesized and isolated in macroscopic quantities.[4,5,6,7] Various fullerene derivatives are promising for the development of diverse fullerenebased materials possessing unique properties for application in materials and biological sciences.[8,9,10,11] methanofullerenes and 20,30-dihydrofuran C60 derivatives (dihydrofuran-fused C60 derivatives), as shown in Fig. 1, are classical fullerene derivatives containing a fused three- or vemembered ring, which have been synthesized in moderate yields via the Bingel–Hirsch reaction[12,13] and transition-metal catalyst-mediated[14,15] or high-speed vibration milling (HSVM).[16]
Methanofullerenes and 20,30-dihydrofuran C60 derivatives, as shown in Fig. 1, are classical fullerene derivatives containing a fused three- or vemembered ring, which have been synthesized in moderate yields via the Bingel–Hirsch reaction[12,13] and transition-metal catalyst-mediated[14,15] or high-speed vibration milling (HSVM).[16]
The experiment was designed to control the selective formation of a single product in a relatively high yield
Summary
Fullerenes have attracted signi cant attention from chemists due to their unique geometric and electronic structures.[1,2,3] To date, the functionalization of fullerenes is of great importance for fullerene chemistry since fullerenes can be synthesized and isolated in macroscopic quantities.[4,5,6,7] Various fullerene derivatives are promising for the development of diverse fullerenebased materials possessing unique properties for application in materials and biological sciences.[8,9,10,11] methanofullerenes and 20,30-dihydrofuran C60 derivatives (dihydrofuran-fused C60 derivatives), as shown in Fig. 1, are classical fullerene derivatives containing a fused three- or vemembered ring, which have been synthesized in moderate yields via the Bingel–Hirsch reaction[12,13] and transition-metal catalyst-mediated[14,15] or high-speed vibration milling (HSVM).[16]. We have selectively synthesized methanofullerenes and 20,30-dihydrofuran C60 derivatives as a single product in each reaction, respectively, in an iodine-base system by controlling the addition sequence and molar ratio of iodine and base, as shown in Scheme 1. E Addition sequence is different from the entries 1 to 11, that is, iodine is added rst followed by the addition of the base.
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