New Routes to Siloles

Significance

Siloles have a low-lying LUMO orbital and are a complementary monomer to the ­aromatic heterocycles (thiophene, pyrrole, furan), which have high-lying HOMOs, for the formation of electronic polymeric materials. This synthesis allows entry to siloles in >70% yield with substitution patterns that were not readily accessible with previous syntheses. In addition the authors have taken a first step with a Migita-Kosugi-Stille coupling reaction to create extended electronic structures. This method should be readily extended to the synthesis of luminescent and electron-accepting molecules and polymers.