Tetrakis(ferrocenylethynyl)ethene: Synthesis, (Spectro)electrochemical and quantum chemical characterisation
| Autor: | Simon Gückel, Paul J. Low, Martin Kaupp, Qiang Zeng, František Hartl, Josef B. G. Gluyas, Kevin B. Vincent |
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| Rok vydání: | 2016 |
| Předmět: |
Quantum chemical
010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Electrolyte 010402 general chemistry Electrochemistry 01 natural sciences Biochemistry 0104 chemical sciences Ion Inorganic Chemistry Crystallography chemistry.chemical_compound Ferrocene Materials Chemistry Oxidation process Physical and Theoretical Chemistry Cyclic voltammetry Dichloromethane |
| Zdroj: | Journal of Organometallic Chemistry. 821:40-47 |
| ISSN: | 0022-328X |
| Popis: | Tetrakis(ferrocenylethynyl)ethene (1) has been prepared in four steps from ethynyl ferrocene (2). In a dichloromethane solution containing 10−1 M NBu4[PF6], only a single oxidation process is observed by cyclic voltammetry, corresponding to the independent oxidation of the four ferrocenyl moieties. However, in dichloromethane containing 10−1 M NBu4[BArF4] electrolyte, where [BArF4]– is the weakly associating anion [B{C6H3(CF3)2-3,5}4]–, four distinct oxidation processes are resolved, although further spectroelectrochemical investigation revealed essentially no through bond interaction between the individual ferrocenyl moieties. Quantum chemical treatment of 1 identified several energetic minima corresponding to different relative orientations of the ferrocenyl moieties and the plane of the all-carbon bridging fragment. Further computational investigation of the corresponding monocation [1]+ supported the notion of charge localisation with no evidence for significant through bond electronic interactions. |
| Databáze: | OpenAIRE |
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