Numerous procedures have been used to produce a variety of hydrogenated fullerenes from C60H2 up to C60H36; in some cases, greater than 36 hydrogens can be added to the fullerene. Many of these methods proceed without regioselectivity and require extensive preparative or semi-preparative HPLC purification resulting in only small amounts of a single isomer. We recently reported a novel method for fullerene hydrogenation using boiling diethylenetriamine[1]. This is an inexpensive, scalable method to produce multigram quantities of pure C3v symmetric C60H18 in excellent yield with no purification necessary. The C60H18 produced has been fully characterized by a combination of 1H and 13C NMR, LD-TOF mass spectrometry and UV-vis spectrophotometry and is identical with the “crown structure” reported by Taylor[2]. In addition, this polyamine chemistry has been utilized for the hydrogenatation of larger fullerenes. The hydrogenation of [70]fullerene does not proceed in a regioselective fashion. A complex mixture of products is produced under standard conditions (with isomers ranging from C70H20 to C70H32+), but as temperature and pressure are increased, there is some evidence for convergence to a single isomer. Giant fullerenes have also been hydrogenated using this chemistry. When a mixture of giant fullerenes are subjected to this chemistry, a variety of hydrogenated giant fullerenes are observed by LD-TOF mass spectrometry.

[1] Briggs, J. B.; Montgomery, M.; Silva, L. L.; Miller, G. P. Org. Lett. 2005, 7, 5553-5555. [2] Darwish, A. D.; Avent, A. G.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Perkin Trans. 2 1996, 10, 2051.