The First Spirobifluorenes Containing Two Binaphthyl Moieties

Alexander G. Russell, Neil S. Spencer, Douglas Philp, Benson M. Kariuki, John S. Snaith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The first spirobifluorenes which comprised of two binaphthyl moieties with silicon and germanium at the site of fusion were synthesized and fully characterized. The compounds were prepared by lithiation of 2,2′-dibromobinaphthyl (78 to -30°C) and subsequent treatment of the dilithio species with 0.5 equiv of silicon tetrachloride or germanium tetrachloride, followed by chromatography over silica gel. X-ray crystallography analysis revealed that both molecules possessed highly distorted structures, which resulted in a low barrier for interconversion between the two atropisomers. The barrier was calculated from the temperature dependency of the nuclear magnetic resonance spectra.

Original languageEnglish (US)
Pages (from-to)5589-5592
Number of pages4
JournalOrganometallics
Volume22
Issue number26
DOIs
StatePublished - Dec 22 2003

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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