Synthesis and redox properties of racemic electroactive polymers containing axially chiral adamantyl segments

A method of introducing chirality directly into a polymer backbone has been developed that employs the dissymmetry of an adamantane derivative with axial chirality. This new chiral adamantane building block was readily functionalized with electroactive thiophene rings using palladium-catalyzed cross-coupling methodology. The two resulting electroactive monomers were electropolymerized to create racemic electroactive polymers containing phenyl-capped oligothiophene segments alternating with chiral adamantyl segments. Synthesis, electrochemistry, and spectroelectrochemistry studies are reported.