The crystal structure of 14-oxo-13,14-seco-5?-cholest-13(18)-en-3?-yl acetate
(2), obtained (in addition to the (E)-?l2-isomer 3) by oxidative
fragmentation of the C(13)-C(14) bond of 14?-hydroxy-5?-cholestan-3?-yl
acetate (1), was determined by X-ray analysis. In addition, the
configurations of the acetoxy derivatives 4-6, formed by the thermal lead
tetraacetate oxidation of 1, were deduced from the relevant 1?-NMR
parameters.
The potential use of amphiphilic fullerene derivatives as a bionanomaterial was investigated by cyclic voltammetry (CV), scanning electron microscopy (SEM), and the ferrous ion oxidation-xylenol orange (FOX) method. Despite the disrupted delocalization of the π-electronic system over the C 60 sphere, its antioxidant capacity remained high for all twelve derivatives. The compounds expressed up to twofold and 5-12-fold better peroxide quenching capacity as compared to pristine C 60 and standard antioxidant vitamin C, respectively. During precipitation and slow evaporation of the solvent, all compounds underwent spontaneous self-assembly giving ordered structures. The size and morphology of the resulting particles depend primarily on the sample concentration, and somewhat on the side chain structure.
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