Reductive alkylation of single-walled carbon nanotubes (SWNTs) using lithium and alkyl halides in liquid ammonia yields sidewall functionalized nanotubes that are soluble in common organic solvents. Atomic force microscopy (AFM) and high-resolution tunneling electron microscopy (HRTEM) of dodecylated SWNTs prepared from raw HiPco nanotubes show that extensive debundling has occurred. GC-MS analysis of the byproduct hydrocarbons demonstrates that alkyl radicals are intermediates in the alkylation step.

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Prolonged hydrogenation of C(60) molecules by reaction with H(2) at elevated temperature and pressure results in fragmentation and collapse of the fullerene cage structure. However, fragments can be preserved by immediate termination of dangling bonds by hydrogen. Here we demonstrate that not only fullerene fragments but also hydrogenated fragmented fullerenes (e.g., C(58)H(40) and C(59)H(40)) can be synthesized in bulk amount by high-temperature hydrogenation of C(60). We confirm successful synthesis of these species by matrix-assisted laser desorption ionization time-of-flight mass spectrometry and complete speciation of the resultant complex fullerene mixtures by high-resolution field desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry.