A Route to Conjugated Monomers and Polymers Incorporating 2,5-Connected Oxazole in the Backbone

Joining of imidazole, pyrimidine, and oxazole to other conjugated core units was explored in pursuit of yielding monomers to synthesize organic semiconducting polymers. Regioregular oxazole-flanked thiophene, benzothiadiazole, naphthalene diimide (NDI), and thienopyrroledione (TPD) were successfully isolated via stannylation of oxazole and the Stille coupling of brominated core units (overall yields ranging from ca. 40 to 60%). From subsequent direct arylation polymerization, NDI/oxazole/TPD-containing regioisomeric polymers were obtained with optical and electrochemical orbital energetics in the semiconducting regime.