Isolation and spectroscopic characterisation of C60F18CF2, the first difluoromethano[60]fullerene

Formation, Isolation, and Spectroscopic Properties of Some Isomers of C60H38, C60H40, C60H42, and C60H44 − Analysis of the Effect of the Different Shapes of Various Helium‐Containing Hydrogenated Fullerenes on Their 3He Chemical Shifts

“…[21,23] When these retention times were reported, the authors stated that ''There is presently no clear explanation for this behaviour.'' [21] In each of C 60 F 2 , C 60 F 4 , C 60 F 6 , C 60 F 8 , [21] C 60 F 16 and C 60 F 18 , [24] all the fluorine atoms are in just one-half of the molecule. Clearly, adding successive pairs of fluorine atoms to just one-half of the molecule should result in a steady increase in polarity through C 60 work indicates that uncertainty exists concerning the precise structure of C 60 F 8 [25] ), and a steady increase in retention time is consistent with a steady increase in polarity.…”

“…[26] The much longer retention time of C 60 F 18 is consistent with its greater polarity. [27] The C s symmetry of C 60 F 16 , [24] the precursor to C 60 F 18 , [26] is lower than the C 3v symmetry of C 60 F 18 , which would account for the still higher polarity of C 60 F 16 .…”

Why fluorinate fullerenes?

“…Characterised derivatives are C 60 F 17 CF 3 , which exists as a dl pair of isomers (31), and a symmetrical isomer (32a), together with symmetrical C 60 F 17 CF 2 CF 3 (32b) the latter probably arising from further:CF 2 insertion into a C-F bond of the CF 3 group [47]. Due to NMR anomalies, some of these compounds were characterised initially as difluoromethyl derivatives.…”

Fluorinated Fullerenes

“…[41] (Remarkably, C 60 F 17 CF 3 showed virtually no resonance for the CF 3 group in the 19 F NMR spectrum, which led to the belief originally that the compound isolated was the isomeric C 60 F 18 CF 2 . [42] ) The CF 2 group inserts into the two most accessible CÀF bonds in the molecule in a 65:35 ratio to give the C s and C 1 compounds, respectively, as shown in Figure 11; the latter component is a thus a chiral mixture. shows the single crystal X-ray structure of the main component.…”