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Synthesis, Isolation, and Trifluoromethylation of Two Isomers of C 84 ‐Based Monometallic Cyanide Clusterfullerenes: Interplay between the Endohedral Cluster and the Exohedral Addends
Author(s) -
Jin Fei,
Wang Song,
Tamm Nadezhda B.,
Yang Shangfeng,
Troyanov Sergey I.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201707298
Subject(s) - reactivity (psychology) , chemistry , endohedral fullerene , cluster (spacecraft) , trifluoromethylation , fullerene , cyanide , crystallography , stereochemistry , trifluoromethyl , metal , carbon fibers , organic chemistry , materials science , medicine , alkyl , alternative medicine , pathology , computer science , programming language , composite number , composite material
As an emerging member of endohedral fullerenes, metal cyanide clusterfullerenes (CYCF) are unique in terms of the encapsulation of a monometallic cluster. To date the reported carbon cages of CYCFs are limited to C 82 and C 76 , and little is known about the chemical reactivity of CYCFs. Herein, two isomers of the first C 84 ‐based CYCFs, YCN@C 84 , were isolated as trifluoromethyl derivatives, including YCN@C 84 (23)(CF 3 ) 18 and three isomers of YCN@C 84 (13)(CF 3 ) 16 , which are based on a unique chiral C 2 ‐C 84 (13) cage. As a common feature of the CF 3 addition patterns, the YCN@C 84 (CF 3 ) 16/18 compounds are stabilized by the formation of isolated C=C bonds and benzenoid rings on the carbon cages. The interplay between the endohedral YCN cluster and the exhohedral CF 3 addends was unveiled according to single‐crystal X‐ray diffraction studies, thus offering new insight into the chemical reactivity of CYCFs.