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Fused‐Pentagon Isomers of C 60 Fullerene Isolated as Chloro and Trifluoromethyl Derivatives
Author(s) -
Vysochanskaya Olga N.,
Brotsman Victor A.,
Goryunkov Alexey A.,
Feiler Christian G.,
Troyanov Sergey I.
Publication year - 2020
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.201905229
Subject(s) - fullerene , buckminsterfullerene , chemistry , cage , trifluoromethyl , carbon fibers , trifluoromethylation , derivative (finance) , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , alkyl , mathematics , combinatorics , composite number , financial economics , economics , composite material
The carbon cage of buckminsterfullerene I h ‐C 60 , which obeys the Isolated‐Pentagon Rule (IPR), can be transformed to non‐IPR cages in the course of high‐temperature chlorination of C 60 or C 60 Cl 30 with SbCl 5 . The non‐IPR chloro derivatives were isolated chromatographically (HPLC) and characterized crystallographically as 1809 C 60 Cl 16 , 1810 C 60 Cl 24 , and 1805 C 60 Cl 24 , which contain, respectively two, four, and four pairs of fused pentagons in the carbon cage. High‐temperature trifluoromethylation of the chlorination products with CF 3 I afforded a non‐IPR CF 3 derivative, 1807 C 60 (CF 3 ) 12 , which contains four pairs of fused pentagons in the carbon cage. Addition patterns of non‐IPR chloro and CF 3 derivatives were compared and discussed in terms of the formation of stabilizing local substructures on fullerene cages. A detailed scheme of the experimentally confirmed non‐IPR C 60 isomers obtained by Stone–Wales cage transformations is presented.