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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Liang et al. (2004) studied this question.
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