High-temperature and photochemical syntheses of C60 and C70 fullerene derivatives with linear perfluoroalkyl chains

Pressure effect on heterogeneous trifluoromethylation of fullerenes and its application

“…S-3). The identification of the HPLC peaks in the traces of crude TMF mixtures was accomplished by their HPLC separation followed by their analysis using APCI mass spectrometry, 19 F NMR and UV-vis spectroscopy. In agreement with earlier results [4,5], the relative retention times of fullerene(CF 3 Table 1) except for the reaction time (30 min for experiments A and 90 min for experiments B).…”

“…Copper powder is commonly used to facilitate the dissociation of perfluoroalkyl iodides and scavenge iodine (it was used for a preparation of some fullerene(C 2 F 5 ) n ) [18][19][20]. In this study, the effect of copper metal on the trifluoromethylation of C 60 with CF 3 I was evaluated.…”

“…HPLC analysis of the crude product obtained from 120 mg of fullerene extract in the GTGS reactor (10 torr of CF 3 I, T hz = 480 8C, L spacer = 10 mm, cold finger used to capture the iodine). Pure C 60 (CF 3 ) 2 was isolated from the crude using HPLC and analyzed by 19 F NMR spectrscopy and HPLC, see inserts. …”

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

“…Such conditions typically favor the formation of PFAFs with a large number of R F substituents, with simple bis-derivatives fullerene(R F ) 2 either absent from crude reaction mixtures or present in trace amounts. [4,5,20,21] Only 1,7-C 60 (CF 3 ) 2 ,[20,22] 1,7-C 60 (C 2 F 5 ) 2 ,[23] and 1,7-C 60 ( i -C 3 F 7 ) 2 [24] have been isolated and characterized using high-temperature heterogeneous synthetic methods. It is notable that previous studies of C 60 halogenation demonstrated that selective synthesis of simple bis-derivatives C 60 Hal 2 (Hal = F, Cl, and Br; iodofullerenes have not been reported) is difficult to achieve while many multisubstituted C 60 Hal n have been prepared (e.g., C 60 F 18 , C 60 F 36 , C 60 F 48 , C 60 Cl 6 , C 60 Cl 24 , and C 60 Br 24 ).…”

In Search of Fullerene‐Based Superacids: Synthesis, X‐ray Structure, and DFT Study of C60(C2F5)5H

“…Perfluoroalkylated fullerenes stand out as chemical platforms for preparation of fullerene acids due to their unique stability, remarkable electrochemical properties, good solubility, and ability to undergo further selective derivatizations. [18] The combination of electron delocalization and steric shielding, relatively low BDEs of fullereneÀH bonds, and unprecedented variety of addition patterns suggests that fullerene(R F ) 2n + 1 H compounds are likely to become a formidable class of superacids of fundamental and practical importance. [19] One of the most exciting prospects is the synthesis of novel, strong yet gentle (non-oxidizing and non-nucleophilic) Brønsted superacids soluble in fluorous solvents.…”