Abstract
AbstractThrough one pot reaction of C60 with organocopper/magnesium reagent ( p‐MeC6H4 )2 CuMgBr or ( m ‐ MeC6 H4 )2‐CuMgBr prepared from CuBr‐Me2S and p‐MeC6H4MgBr or m‐MeC6H4 MgBr and subsequent quenching with aqueous NH4Cl, two pentaarylated [ 60 ] fullerene derivatives (p‐MeC6H4)5 C60H (1) and (m‐MeC6H4)5 C60H (2) have been synthesized in 94% and 96% yields, respectively. While known compound 1 prepared via this improved method is unambiguously identified, new compound 2 is fully characterized by elemental analysis, IR, UV‐vis, 1H NMR and 13C NMR spectroscopies. Additionally, electrochemical study shows that the two [60] fullerene derivatives 1 and 2 in dichloromethane solution display two sequential one‐electron reductions which are shifted by about 0.4 V towards more negative potential values with respect to free C60. Such remarkable cathodic shift is attributed to the multiple breakage of the double‐bond conjugation within the Fullerene core.
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