A Novel Synthesis Strategy for Poly(Arylene-Vinylene) Derivatives by Elemental Sulfur-Mediated Polyolefination

Herein, a new synthetic access to poly(arylene-1,2-diarylvinylene) (PAV-DA) derivatives is presented by a novel polyolefination of bifunctional N-tosylhydrazones using base-activated elemental sulfur. PAV-DAs are particularly interesting due to their aggregation-induced emission (AIE) properties, resulting in high solid-state photoluminescence quantum yields. The presented procedure allows the successful synthesis of eight homopolymers and two copolymers with different arylene backbones and aryl side chains from easily accessible monomers, not requiring the use of expensive or highly hazardous materials. The polymers are obtained in good yields and number average molecular weights up to 26.9 kDa. Thermal analysis reveals exceptionally high thermal stability with degradation temperatures as high as 541 °C and glass transition temperatures of up to 263 °C. Furthermore, it is found that the polymer properties are easily adjustable via copolymerization.