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Isolation and Structure Determination of a Missing Endohedral Fullerene La@C 70 through In Situ Trifluoromethylation
Author(s) -
Wang Zhiyong,
Aoyagi Shinobu,
Omachi Haruka,
Kitaura Ryo,
Shinohara Hisanori
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201508082
Subject(s) - trifluoromethylation , fullerene , metallofullerene , endohedral fullerene , chemistry , crystallography , materials science , organic chemistry , alkyl , trifluoromethyl
D 5 h ‐symmetric fullerene C 70 ( D 5 h ‐C 70 ) is one of the most abundant members of the fullerene family. One longstanding mystery in the field of fullerene chemistry is whether D 5 h ‐C 70 is capable of accommodating a rare‐earth metal atom to form an endohedral metallofullerene M@ D 5 h ‐C 70 , which would be expected to show novel electronic properties. The molecular structure of La@C 70 remains unresolved since its discovery three decades ago because of its extremely high instability under ambient conditions and insolubility in organic solvents. Herein, we report the single‐crystal X‐ray structure of La@C 70 (CF 3 ) 3 , which was obtained through in situ exohedral functionalization by means of trifluoromethylation. The X‐ray crystallographic study reveals that La@C 70 (CF 3 ) 3 is the first example of an endohedral rare‐earth fullerene based on D 5 h ‐C 70 . The dramatically enhanced stability of La@C 70 (CF 3 ) 3 compared to La@C 70 can be ascribed to trifluoromethylation‐induced bandgap enlargement.