Synthesis of [all]-S,S-Dioxide Oligothiophenes Using HOF⋅CH3CN


  • This work was supported by the Israel Science Foundation (Jerusalem, Israel).


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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.