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C 2 Isomers of C 84 F 40 and C 84 F 44 Are Cuboid and Contain Benzenoid and Naphthalenoid Aromatic Patches
Author(s) -
Darwish Adam D.,
Martsinovich Natalia,
Street Joan M.,
Taylor Roger
Publication year - 2005
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.200500403
Subject(s) - octahedron , crystallography , cuboid , chemistry , fullerene , derivative (finance) , aromaticity , stereochemistry , molecule , crystal structure , organic chemistry , geometry , mathematics , financial economics , economics
A 1:1 mixture of C 84 F 40 and C 84 F 44 , both derived from the D 2 (IV) isomer, has been isolated from the fluorination of [84]fullerene with either MnF 3 or CoF 3 at 500 °C. The 1D and 2D COSY 19 F NMR spectra showed that each derivative is cuboid, having benzenoid rings at four of the six octahedral sites; the two remaining sites have naphthalenoid rings for C 84 F 40 , and two slightly offset benzenoid rings for C 84 F 44 . The benzenoid rings each have six adjacent sp 3 ‐hybridised carbon atoms whilst the naphthalenoid moieties have eight, thus facilitating full delocalisation. In terms of the number and size of aromatic patches, C 84 F 44 is the most aromatic fullerene derivative yet isolated.