Solution-phase perfluoroalkylation of C60 leads to efficient and selective synthesis of bis-perfluoroalkylated fullerenes

A solution-phase perfluoroalkylation of C60 with a series of RFI reagents was studied. The effects of molar ratio of the reagents, reaction time, and presence of copper metal promoter on fullerene conversion and product composition were evaluated. Ten aliphatic and aromatic RFI reagents were investigated (CF3I, C2F5I, n-C3F7I, i-C3F7I, n-C4F9I, (CF3)(C2F5)CFI, n-C8F17I, C6F5CF2I, C6F5I, and 1,3-(CF3)2C6F3I) and eight of them (except for C6F5I and 1,3-(CF3)2C6F3I) were found to add the respective RF groups to C60 in solution. Efficient and selective synthesis of C60(RF)2 derivatives was developed.

Graphical abstractSolution-phase perfluoroalkylation of C60 with a series of RFI reagents was studied under variety of conditions and resulted in the development of selective syntheses of bis-adducts.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Efficient perfluoroalkylation of C60 with RFI reagents under homogeneous conditions. ► Strong effect of reagent ratio, reaction time, and copper promoter on product composition. ► Selective synthesis of bisadducts is based on “low-conversion” reaction regime.