Electron affinities of [5,6]-open and [5,6]-closed adducts of trifluoromethylfullerene C s -C 70 (CF 3 ) 8 : even one bond matters!
Alexey V Rybalchenko
1
,
Marina G Apenova
1
,
Olesya Semivrazhskaya
1
,
Nikita M Belov
1
,
Vitaliy Markov
1
,
Sergey Troyanov
1
,
Ilya Ioffe
1
,
Natalia Lukonina
1
,
Lev N. Sidorov
1
,
A. Goryunkov
1
Publication type: Journal Article
Publication date: 2016-02-01
scimago Q1
wos Q1
SJR: 1.106
CiteScore: 10.6
Impact factor: 5.6
ISSN: 00134686, 18733859
General Chemical Engineering
Electrochemistry
Abstract
Despite trifluoromethylfullerene Cs-C70(CF3)8 has a multitude of available reaction sites, [2 + 1] cycloaddition of CX2 moieties (X = F and p-MeOC6H4) proceeds regioselectively at a particular [5,6]-bond. Depending on the nature of X, the resulting derivative can be either [5,6]-open (i.e., the said C C bond is cleaved) or [5,6]-closed, and this structural detail, seemingly insignificant for a molecule that large, brings about a remarkable 0.6 eV difference in the electron affinity, as revealed by electrochemical studies. Synthesis, structural and electrochemical elucidation of the C70(CF3)8(CX2) compounds are discussed, as well as electrochemically promoted switching of the electronic properties based on disruption of the conjugated 62π-electron system into the isolated 32 and 28π-electron fragments upon closing the [5,6]-bond.
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Rybalchenko A. V. et al. Electron affinities of [5,6]-open and [5,6]-closed adducts of trifluoromethylfullerene C s -C 70 (CF 3 ) 8 : even one bond matters! // Electrochimica Acta. 2016. Vol. 191. pp. 980-986.
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Rybalchenko A. V., Apenova M. G., Semivrazhskaya O., Belov N. M., Markov V., Troyanov S., Ioffe I., Lukonina N., Sidorov L. N., Magdesieva T. V., Goryunkov A. Electron affinities of [5,6]-open and [5,6]-closed adducts of trifluoromethylfullerene C s -C 70 (CF 3 ) 8 : even one bond matters! // Electrochimica Acta. 2016. Vol. 191. pp. 980-986.
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TY - JOUR
DO - 10.1016/j.electacta.2016.01.125
UR - https://doi.org/10.1016/j.electacta.2016.01.125
TI - Electron affinities of [5,6]-open and [5,6]-closed adducts of trifluoromethylfullerene C s -C 70 (CF 3 ) 8 : even one bond matters!
T2 - Electrochimica Acta
AU - Rybalchenko, Alexey V
AU - Apenova, Marina G
AU - Semivrazhskaya, Olesya
AU - Belov, Nikita M
AU - Markov, Vitaliy
AU - Troyanov, Sergey
AU - Ioffe, Ilya
AU - Lukonina, Natalia
AU - Sidorov, Lev N.
AU - Magdesieva, Tatiana V.
AU - Goryunkov, A.
PY - 2016
DA - 2016/02/01
PB - Elsevier
SP - 980-986
VL - 191
SN - 0013-4686
SN - 1873-3859
ER -
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BibTex (up to 50 authors)
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@article{2016_Rybalchenko,
author = {Alexey V Rybalchenko and Marina G Apenova and Olesya Semivrazhskaya and Nikita M Belov and Vitaliy Markov and Sergey Troyanov and Ilya Ioffe and Natalia Lukonina and Lev N. Sidorov and Tatiana V. Magdesieva and A. Goryunkov},
title = {Electron affinities of [5,6]-open and [5,6]-closed adducts of trifluoromethylfullerene C s -C 70 (CF 3 ) 8 : even one bond matters!},
journal = {Electrochimica Acta},
year = {2016},
volume = {191},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.electacta.2016.01.125},
pages = {980--986},
doi = {10.1016/j.electacta.2016.01.125}
}