Open AccessIsolation and structure determination of missing fullerenes Gd@C 74 (CF 3 ) n through in situ trifluoromethylation
Author(s) -
Ayano Nakagawa,
Shinobu Aoyagi,
Haruka Omachi,
Katsuma Ishino,
Makiko Nishino,
Jérémy Rio,
Christopher P. Ewels,
Hisanori Shinohara
Publication year - 2018
Publication title -
royal society open science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.84
H-Index - 51
ISSN - 2054-5703
DOI - 10.1098/rsos.181015
Subject(s) - trifluoromethylation , fullerene , trifluoromethyl , chemistry , structural isomer , dissolution , crystallography , density functional theory , molecular orbital , computational chemistry , molecule , analytical chemistry (journal) , stereochemistry , organic chemistry , alkyl
Our trifluoromethyl functionalization method enables the dissolution and isolation of missing metallofullerenes of Gd@C 74 (CF 3 ) n . After multi-stage high-performance liquid chromatography purification, Gd@C 74 (CF 3 ) 3 and two regioisomers of Gd@C 74 (CF 3 ) are isolated. X-ray crystallographic analysis reveals that all of the isolated metallofullerenes react with CF 3 groups on pentagons of the D 3 h -symmetry C 74 cages. Highest occupied molecular orbital-lowest unoccupied molecular orbital gaps of these trifluoromethylated derivatives, estimated by absorption spectra, are in the range 0.71–1.06 eV, consistent with density functional calculations.