Electron affinities of [5,6]-open and [5,6]-closed adducts of trifluoromethylfullerene Cs-C70(CF3)8: even one bond matters!
| Autor: | Ilya N. Ioffe, Natalia S. Lukonina, Tatiana V. Magdesieva, Alexey V. Rybalchenko, Alexey A. Goryunkov, Sergey I. Troyanov, Olesya O. Semivrazhskaya, Nikita M. Belov, Vitaliy Yu. Markov, Lev N. Sidorov, Marina G. Apenova |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Stereochemistry General Chemical Engineering Conjugated system 010402 general chemistry Electrochemistry 01 natural sciences Cycloaddition 0104 chemical sciences Adduct Crystallography chemistry.chemical_compound chemistry Electron affinity Molecule Cyclic voltammetry Derivative (chemistry) |
| Zdroj: | Electrochimica Acta. 191:980-986 |
| ISSN: | 0013-4686 |
| DOI: | 10.1016/j.electacta.2016.01.125 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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