Synthesis of [all]‐<i>S</i>,<i>S</i>‐Dioxide Oligothiophenes Using HOF⋅CH₃CN

Abstract

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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z501681_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.