Reactivity of silyl monomers for the oxidative polymerization of phenyleneunits

Oxidative coupling of silyl monomers containing phenylene units was perform ed electrochemically and chemically using FeCl3 as oxidant. 2,5-Trimethylsi lyl-1,1-dihexoxybenzene led to poly (2,5-dihexoxyparaphenylene) with a degr ee of polymerization higher than the one obtained upon oxdative coupling of non silyl monomers. The coupling reaction was however moderately improved in the case of 3,6-bis-dimethylsilyl(N-n-butylcarbazole). The role of the s ilyl Substituents during the oxidative polymerization is discussed.