2024 Volume 82 Issue 6 Pages 605-612
Functional organic materials play an important role in the innovation of science and technology as well as in updating our daily lives. Therefore, developing new synthetic methods that enable to create new functional materials is attracting increasing attention. This article describes the synthesis of dibromoindenes and tetrabromoindacenes, which are important synthetic modules in synthetic organic chemistry, based on the Friedel-Crafts type cyclization reaction using Lewis acid or Brønsted acid. Our protocol features the absence of special care for air and moisture and facile derivatization from commercially available starting materials. These dibromoindenes and tetrabromoindacenes have served as precursors to obtain a new family of carbon-bridged oligo(phenylenevinylene)s (COPVs) which have broad scope of substituents on the bridging carbon atoms and were impossible to obtain using the previous methods. Developments on the creation of novel photofunctional materials based on COPV, such as near infrared light emitting materials and photonic crystals, will also be introduced.
