Synthesis of two pentaarylated [ 60 ]fullerene derivatives Ar5C60-H (Ar = p-MeC6H4, m-MeC6H4) and their novel electrochemical properties

• 来源期刊: 中国化学（英文版）
• 年，卷（期）: 2000,（3）
• 页码范围: 395-401
• 页数: 7页
• 语种: 英文

摘要

Through one pot reaction of C60 with organocopper/magnesium reagent ( p -MeC6 H4 )2 CuMgBr or ( m- MeC6 H4 )2-CuMgBr prepared from CuBr· Me2S and p-MeC6H4MgBr or m-MeC6H4MgBr and subsequent quenching with aqueous NHeCl, two pentaarylated [60] fullerene derivatives (p-MeC6H4)5C60H (1) and (m-MeC6H4)5C60H (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.