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Isolation and Structural X‐ray Investigation of Perfluoroalkyl Derivatives of Six Cage Isomers of C 84
Author(s) -
Tamm Nadezhda B.,
Sidorov Lev N.,
Kemnitz Erhard,
Troyanov Sergey I.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901596
Subject(s) - chemistry , molecule , toluene , x ray , hexane , stereochemistry , crystallography , crystal structure , organic chemistry , physics , quantum mechanics
Perfluoroalkylation of a higher fullerene mixture with CF 3 I or C 2 F 5 I, followed by HPLC separation of CF 3 and C 2 F 5 derivatives, resulted in the isolation of several C 84 (R F ) n ( n =12, 16) compounds. Single‐crystal X‐ray crystallography with the use of synchrotron radiation allowed structure elucidation of eight C 84 (R F ) n compounds containing six different C 84 cages (the number of the C 84 isomer is given in parentheses): C 84 (23)(C 2 F 5 ) 12 ( I ), C 84 (22)(CF 3 ) 16 ( II ), C 84 (22)(C 2 F 5 ) 12 ( III ), C 84 (11)(C 2 F 5 ) 12 ( IV ), C 84 (16)(C 2 F 5 ) 12 ( V ), C 84 (4)(CF 3 ) 12 ( VI with toluene and VII with hexane as solvate molecules), and C 84 (18)(C 2 F 5 ) 12 ( VIII ). Whereas some connectivity patterns of C 84 isomers (22, 23, 11) had previously been unambiguously confirmed by different methods, derivatives of C 84 isomers numbers 4, 16, and 18 have been investigated crystallographically for the first time, thus providing direct proof of the connectivity patterns of rare C 84 isomers. General aspects of the addition of R F groups to C 84 cages are discussed in terms of the preferred positions in the pentagons under the formation of chains, pairs, and isolated R F groups.