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Addition of S ‐Heterocyclic Carbenes to Fullerenes: Formation and Characterization of Dithiomethano‐Bridged Derivatives
Author(s) -
Kako Masahiro,
Arikawa Yuki,
Kanzawa Shinji,
Yamada Michio,
Maeda Yutaka,
Furukawa Makoto,
Akasaka Takeshi
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201900064
Subject(s) - chemistry , fullerene , cycloaddition , adduct , density functional theory , fullerene chemistry , medicinal chemistry , characterization (materials science) , stereochemistry , computational chemistry , catalysis , organic chemistry , nanotechnology , materials science
The reactions of novel S ‐heterocyclic carbenes (SHCs), which were prepared by the cycloaddition of disilenes and digermenes to CS 2 , with C 60 and Sc 3 N@ I h ‐C 80 afforded the corresponding methano‐bridged fullerenes. The [6,6]‐closed and [6,6]‐open structures were characterized for the SHC adducts of C 60 and Sc 3 N@ I h ‐C 80 , respectively. These derivatives exhibited relatively low oxidation potentials, indicative of the electron‐donating effects of the SHC addends. The electronic properties of the SHC derivatives were clarified by the density functional theory calculations.