Electron affinities of [5,6]-open and [5,6]-closed adducts of trifluoromethylfullerene Cs-C70(CF3)8: even one bond matters!статья

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Дата последнего поиска статьи во внешних источниках: 20 июля 2016 г.

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[1] Electron affinities of [5,6]-open and [5,6]-closed adducts of trifluoromethylfullerene cs-c70(cf3)8: even one bond matters! / A. V. Rybalchenko, M. G. Apenova, O. O. Semivrazhskaya et al. // Electrochimica Acta. — 2016. — Vol. 191. — P. 980–986. Highlights • Crucial influence of open-closed skeletal transitions on the electronic properties of fullerene was demonstrated. • Electrochemically promoted switching of 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 in question. • Regioselective near-equatorial cycloproponation of trifluoromethylfullerene Cs-C70(CF3)8 was elaborated. • More compact alternatives promising molecular switching capabilities can be found within the family of pyramidalized polyenes. 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 Csingle bondC 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. Keywords methylenated fullerene; electrochemically promoted switching; cyclic voltammetry; DFT calculation; skeletal transformation. [ DOI ]

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