Electrochemical Properties of 9,9′-Spiro-Bifluorenes Containing Group 14 Elements (C, Si, Ge, Sn)

Tatiana Golub-Sedinkin, Ajith C. Herath, Robert West, James Y. Becker

Research output: Contribution to journalArticlepeer-review

1 Scopus citations


Cyclic voltammograms of four spiro-bifluorenes involving C (I), Si (II), Ge (III) and Sn (IV) as the central atom were recorded in acetonitrile-dichloromethane. Each substrate afforded one irreversible oxidation wave (between 1.7 to 1.9 V, vs. Ag/AgCl) and one irreversible reduction wave between −2.0 to −2.3 V (except for the Ge derivative III that showed a second irreversible reduction wave). Controlled potential anodic oxidation was executed for II–IV on a Pt anode. Surprisingly, each one of the substrates behaved differently: II yielded biphenyl (92 %) as the major product; III afforded moderate yields of a germafluorene dimer containing Ge−Ge bond (35 %) and 1,3,5-triphenylbenzene 10 (22 %), and IV formed the aromatic derivative 10 as the major product (76 %). In all cases, chlorinated products were formed too. A plausible mechanism for the formation of the variety of products is suggested.

Original languageEnglish
Pages (from-to)4252-4256
Number of pages5
Issue number16
StatePublished - 16 Aug 2019


  • 9.9′-spiro-germabifluorene
  • 9.9′-spiro-silabifluorene
  • 9.9′-spiro-stannabifluorene
  • controlled potential oxidation
  • cyclic voltammetry

ASJC Scopus subject areas

  • Catalysis
  • Electrochemistry


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