Abstract
A direct, selective functionalization of C60 with amides and lactams has been developed. This efficient photochemical approach utilizes a diverse variety of radicals deriving from secondary and tertiary carboxy-, sulfonyl-, phosphoramides as well as lactams through a hydrogen atom transfer (HAT) process mediated by tetrabutylammonium decatungstate [(n-Bu4N)4W10O32]. The single addition of these carbon-centered radicals to [60]fullerene proceeded smoothly to produce a novel class of previously unexplored fullerene-based materials. Important structural insight, such as the rotational energy barrier of the amide C(O)–N bond, for these nanostructures is provided and has been experimentally determined by the use of Dynamic NMR spectroscopy. A mechanism for this new reaction has been proposed based mainly on the structure of reaction products and kinetic H/D isotope effect studies.
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