ИСТИНА

The compound S6-C60(CF3)12 is the most synthetic available poly(trifluoromethyl)fullerene. However further synthetic applicability of the compound is restricted by its very low solubility in most organic solvents [1]. The only example of successful functionalization is chlorination of S6-C60(CF3)12 in SbCl5 media yielding mixed chloro- and trifluoromethylderivative S6-C60(CF3)12Cl12 [2]. Here, we report the first results of hydrogenation of S6-C60(CF3)12 via reaction with either 9,10-dihydroantracene or NaBH4. The crystalline S6-C60(CF3)12 was prepared by the known method using an ampoule reaction of C60 with CF3I [1] and recrystallizated from hot odichlorobenzene. Purified sample of S6-С60(CF3)12 was characterized by IR, NMR 19F spectroscopy and MALDI mass spectrometry. Hydrogenation of S6-C60(CF3)12 with melted 9,10-dihydroantracene was performed in sealed tube at heating under argon atmosphere. Unlikely starting material, prepared product is soluble in toluene/hexane mixtures. According to MALDI mass spectral and HPLC analyses, the high temperature hydrogenation of S6-C60(CF3)12 leads to complex mixture of hydrogenated trifluoromethylfullerenes with partial loss of CF3 groups characterized by composition of C60(CF3)nHm, where n=8–12 and m=8–18. Treatment of S6-C60(CF3)12 by NaBH4 at moderate temperature results in selective formation of dodecahydrodenated derivative C60(CF3)12H12 according to MALDI MS data. The synthesized product was HPLC purified and characterized by means of MS MALDI, IR, UV/Vis, NMR spectroscopes. Possible attachment moieties of hydrogen atoms within C60(CF3)12H12 were proposed on basis of NMR data and quantum chemical calculations at the DFT level of theory. References I. Troyanov, A. Dimitrov, 1. E. Kemnitz, Angew. Chem. Int. Ed. (2006) 45, 1971. 2. S.I. Troyanov, E. Kemnitz, Mendeleev Commun. (2008) 18, 27.