Difluoromethylenation of fullerene C70 provides isomeric diversity and availability of equatorial [5,6]-homofullerene C70(CF2)

Авторы: Brotsman Victor A., Lukonina Natalia S., Malkin Nikita A., Rybalchenko Alexey V., Belov Nikita M., Goryunkov Alexey A.
Журнал: Physical Chemistry Chemical Physics
Том: 24
Год издания: 2022
Издательство: Royal Society of Chemistry
Местоположение издательства: United Kingdom
Первая страница: 16816
Последняя страница: 16826
DOI: 10.1039/d2cp01922a
Аннотация: We report synthesis, isolation, and spectroscopic characterization of the novel [5,6]-open C70(CF2) isomer III along with the already known [6,6]-closed and [6,6]-open C70(CF2) isomers I and II. The compounds were obtained in a ratio of I : II : III = 4 : 6 : 1 by means of thermal treatment of C70 fullerene with sodium chlorodifluoroacetate. This product composition is explained with the use of quantum chemical calculations that identify the reaction pathway as a two-stage nucleophilic cyclopropanation rather than the previously postulated carbene addition. We further report the first cyclic voltametric studies for the whole set of isomers of C70(CF2). Together with the DFT data, they demonstrate that the LUMO is stabilized in both isomer II ([6,6]-open) and III ([5,6]-open) by 0.1 eV with respect to the pristine C70, and isomer III has the lowest reorganization energy of all.
Добавил в систему: Горюнков Алексей Анатольевич

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