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Synthesis, Spectroscopic and Electrochemical Characterization, and DFT Study of Seventeen C 70 (CF 3 ) n Derivatives ( n =2, 4, 6, 8, 10, 12)
Author(s) -
Popov Alexey A.,
Kareev Ivan E.,
Shustova Natalia B.,
Lebedkin Sergey F.,
Strauss Steven H.,
Boltalina Olga V.,
Dunsch Lothar
Publication year - 2007
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.200700970
Subject(s) - cyclic voltammetry , chemistry , electrochemistry , spectroscopy , quantum chemical , nuclear magnetic resonance spectroscopy , crystallography , analytical chemistry (journal) , stereochemistry , molecule , electrode , organic chemistry , physics , quantum mechanics
Eight new C 70 (CF 3 ) n derivatives ( n =2, 6, 10, 12) have been synthesized and characterized by UV/Vis and 19 F NMR spectroscopy, cyclic voltammetry, and quantum chemical calculations at the DFT level of theory. Nine previously known derivatives of C 70 (CF 3 ) n with n =2–12 were also studied by cyclic voltammetry (and seven of them by UV/Vis spectroscopy for the first time). Most of the 17 compounds exhibited two or three reversible reductions at scan rates from 20 mV s −1 up to 5.0 V s −1 . In general, reduction potentials for the 0/− couple are shifted anodically relative to the C 70 0/− couple. However, the 0/− E 1/2 values for a given composition are strongly dependent on the addition pattern of the CF 3 groups. The data show that the addition pattern is as important, if not more important in some cases, than the number of substituents, n , in determining E 1/2 values. An analysis of the DFT‐predicted LUMOs indicates that addition patterns that have non‐terminal double bonds in pentagons result in derivatives that are strong electron acceptors.