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

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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