Synthesis of [all]-S,S-dioxide oligothiophenes using HOF·CH 3CN

Elizabeta Amir*, Shlomo Rozen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

73 Scopus citations

Abstract

(Chemical Equation Presented) Nonaromatic stable polyenes are obtained by dioxygenation of oligothiophenes using HOF·CH3CN prepared in situ by passing F2 through aqueous acetonitrile (see scheme). These fully S,S-dioxygenated derivatives have a considerably smaller HOMO-LUMO gap than the parent compounds; furthermore, in the solid state they tend to form favorable π-π stacking interactions, unlike most non-oxidized oligothiophenes which adopt the "herringbone" motif.

Original languageEnglish
Pages (from-to)7374-7378
Number of pages5
JournalAngewandte Chemie - International Edition
Volume44
Issue number45
DOIs
StatePublished - 1 Dec 2005

Keywords

  • Fluorine
  • Hypofluorous acid
  • Oligomers
  • Oxygenation thiophenes

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