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Synthesis and spectral electrochemical properties of a symmetrical tin-bridged [3.3]ferrocenophane

Organometallics, ISSN: 0276-7333, Vol: 32, Issue: 10, Page: 2893-2901
2013
  • 9
    Citations
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  • 9
    Captures
  • 1
    Mentions
  • 0
    Social Media
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  • Citations
    9
    • Citation Indexes
      9
  • Captures
    9
  • Mentions
    1
    • News Mentions
      1
      • News
        1

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Synthesis and characterization of a polyferrocenyldistannane

  Introduction            Since its discovery, the ferrocene moiety has often been used in the modification of molecular and polymeric structure. This is due, in part, to

Article Description

The symmetrical bisferrocene 1,1,14,14-tetra-n-butyl-2,2,13,13,15,15,26,26- octamethyl-1,2,13,14,15,26-hexastanna[3.3]ferrocenophane ([(η- CH)Fe(η-CH SnMeSn(n-Bu)SnMe)], 8) was synthesized in good yield (82%) from the reductive coupling reaction of 1,1′-bis(dimethylstannyl)ferrocene, 6, with one equivalent of di-n-butylbis(diethylamino) stannane, 7a, at 0 C in diethyl ether solution. Compound 8 is stable to ambient light but decomposes in the presence of moisture or chlorinated solvents. The title compound 8 was characterized by NMR ( H, C, Sn, Sn) spectroscopy, HRMS, and elemental analysis. A statistical model to account for the Sn/Sn coupling patterns, observed in both the Sn and Sn NMR spectra, was undertaken and is a good fit to experimental data. Investigations by UV-vis spectroscopy display a visible d-d transition at λ at 455 nm (ε = 74 L mol cm), while cyclic voltammetry reveals two reversible oxidation events at 0.01 and 0.23 V (relative to the ferrocene/ferrocenium couple), indicative of strong electronic communication between the ferrocene units. A DFT analysis of compound 8 supports the symmetrical nature of the molecule with a calculated intramolecular distance of 8.5 Å between iron centers. This is the first example of a [3.3]ferrocenophane bearing three σ-conjugated group 14 spacers between the ferrocene units. Furthermore, an improved route to 1,1,2,2- tetramethyldistannanediyl[2]ferrocenophane 4a has been found, through an intermolecular dehydrogenative coupling of 6 with catalytic amounts of Pd (dba), that leads to superior yields of 4a over previously published protocols. © 2013 American Chemical Society.

Bibliographic Details

Jon Ward; Saif Al-Alul; Daniel A. Foucher; Matthew W. Forbes; Timothy E. Burrow

American Chemical Society (ACS)

Chemistry

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