T_h-C₆₀F₂₄

Abstract

The regioselective fluorination of Th-C60Br24 with XeF2 in anhydrous HF at 25 degrees C produced Th-C60F24, which is isostructural with Th-C60Br24. The compound, the first example of a fluorofullerene with a noncontiguous pattern of F-bearing sp3 C atoms, was characterized by EI and ESI mass spectrometry and by 19F NMR (single resonance at delta -144 for all 24 F atoms), 13C NMR (two resonances at delta 145.9 (C=C) and delta 83.5 (C-F; JCF = 212 Hz), and FTIR spectroscopy. DFT calculations revealed that at least two other isomers of C60F24 are more stable than Th-C60F24 by >/=280 kJ mol-1, demonstrating that Th-C60F24 is a kinetically stable fluorofullerene.

Seven‐Minute Synthesis of Pure Cs‐C60Cl6 from [60]Fullerene and Iodine Monochloride: First IR, Raman, and Mass Spectra of 99 mol % C60Cl6

“…[7] Subsequent papers by others reported the use of C 60 Cl 6 to prepare organic derivatives of C 60 . [14][15][16] It is possible that chlorofullerenes could also be used to prepare new inorganic fullerene derivatives under mild conditions (a recent, related example involving a bromofullerene is the transformation of T h -C 60 Br 24 to kinetically-stable T h -C 60 F 24 at 25 8C [17] ). However, significant progress in the use of chlorofullerene synthons Abstract: Three previously reported procedures for the synthesis of pure C s -C 60 Cl 6 from C 60 and ICl dissolved in benzene or 1,2-dichlorobenzene were shown to actually yield complex mixtures of products that contain, at best, 54-80 % C s -C 60 Cl 6 based on HPLC integrated intensities.…”

“…We recently observed adduct-ion formation in an LDI/MALDI-MS study of the pure fluorofullerene C 60 F 18 . In addition to the C 60 F 18 À molecular ion and the C 60 F 17 À fragment ion, the C 60 F 19 À adduct ion was also observed (its intensity was 10 % of the intensity of the molecular ion). [32] Positive-and negative-ion DCTB-MALDI mass spectra for unpurified (i.e., crude) samples 1-4 were recorded under similar laser-fluence conditions, and the relative intensities of the observed ions were reproducible to within 10-15 %.…”

Novel addition in trifluoromethylation of [70]fullerene

“…However this group have recently used exactly the opposite argument (i.e. kinetic stability) to account for the isolation of T h C 60 F 24 , calculated to be some 340 kJ mol À1 less stable than other isomers [29].…”

Reaction of C60 with KMnF4

“…This is in contrast to the contiguous structures of C 3v -C 60 F 18 [6], D 5d -C 60 F 20 [40], C 1 -C 60 F 36 [9], T-C 60 F 36 [41], C 2 -C 70 F 38 [42], and D 3 -C 74 F 38 [43]. The only other fluorofullerene that has been shown to have isolated C(sp 3 ) atoms is T h -C 60 F 24 [44], and it is not a thermodynamically stable addition pattern. It is a kinetically stable isomer prepared by Br/F substitution of T h -C 60 Br 24 at 25 8C [44].…”