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Synthesis of two pentaarylated [60]fullerene derivatives Ar 5 C 60 ‐H (Ar = p ‐MeC 6 H 4 , m ‐MeC 6 H 4 ) and their novel electrochemical properties
Author(s) -
LiCheng Song,
PengChong Liu,
QingMei Hu,
Fiero Zanello,
Marco Fontam
Publication year - 2000
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20000180325
Subject(s) - chemistry , fullerene , electrochemistry , dichloromethane , reagent , aqueous solution , proton nmr , carbon 13 nmr , quenching (fluorescence) , elemental analysis , fullerene chemistry , medicinal chemistry , stereochemistry , inorganic chemistry , organic chemistry , fluorescence , physics , electrode , quantum mechanics , solvent
Through one pot reaction of C 60 with organocopper/magnesium reagent ( p ‐MeC 6 H 4 ) 2 CuMgBr or ( m ‐ MeC 6 H 4 ) 2 ‐CuMgBr prepared from CuBr‐Me 2 S and p ‐MeC 6 H 4 MgBr or m ‐MeC 6 H 4 MgBr and subsequent quenching with aqueous NH 4 Cl, two pentaarylated [ 60 ] fullerene derivatives ( p‐ MeC 6 H 4 ) 5 C 60 H (1) and ( m ‐MeC 6 H 4 ) 5 C 60 H (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, 1 H NMR and 13 C 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 C 60 . Such remarkable cathodic shift is attributed to the multiple breakage of the double‐bond conjugation within the Fullerene core.