Carbon-Rich trinuclear octamethylferrocenophanes

Max Roemer, Duncan A. Wild, Alexandre N. Sobolev, Brian W. Skelton, Gareth L. Nealon, Matthew J. Piggott, George A. Koutsantonis

Research output: Contribution to journalArticle

Abstract

Several trinuclear ferrocenes are obtained by Friedel–Crafts reaction of octamethylferrocene with ferrocenoyl chloride and subsequent modifications. 1,1′-Diferrocenoyloctamethylferrocene (3) is transformed to the divinyl derivative (4a) by reaction with MeLi and AlCl3. The reactive 4a cyclizes spontaneously to a [4]ferrocenophane with buta-1,3-diene handle (5) or in the presence of AlCl3 to a [3]ferrocenophane with propene handle (6). Structure assignments are supported by X-ray crystallography and NMR spectroscopy, and mechanisms are proposed. Electrochemical behavior of the compounds was investigated with cyclic voltammetry, and assignments of the redox processes were carried out with the aid of density functional theory calculations. The synthesized compounds and demonstrated transformations represent useful tools for preparation of materials for charge-transport studies in metal−molecule−metal junctions.
Original languageEnglish
Pages (from-to)3789-3799
Number of pages11
JournalInorganic Chemistry
Volume58
Issue number6
Early online date5 Mar 2019
DOIs
Publication statusPublished - 18 Mar 2019
Externally publishedYes

Keywords

  • Ferrocene
  • Octamethylferrocene
  • Ferrocenophanes
  • Electrochemistry
  • Cyclisation
  • C-C bond formation

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    Roemer, M., Wild, D. A., Sobolev, A. N., Skelton, B. W., Nealon, G. L., Piggott, M. J., & Koutsantonis, G. A. (2019). Carbon-Rich trinuclear octamethylferrocenophanes. Inorganic Chemistry, 58(6), 3789-3799. https://doi.org/10.1021/acs.inorgchem.8b03389