Abstract
A new silicon-containing bicyclic monomer 5-trimethylsilylbicyclo[2.2.2]oct-2-ene has been synthesized, and its metathesis polymerization and gas transport properties of the polymer based on it have been studied. The monomer is synthesized by the two-step scheme using the Diels–Alder reaction from 1,3-cyclohexadiene and vinyltrichlorosilane followed by methylation with a Grignard reagent. The resulting 5-trimethylsilylbicyclo[ 2.2.2]oct-2-ene is inactive in metathesis homopolymerization in the presence of first- and second- generation Grubbs catalysts and a Hoveyda–Grubbs catalyst, but it slowly polymerizes when norbornene is present in the reaction mixture. The high-molecular-mass copolymer (Mw = 3.0 × 105, Mw/Mn = 2.8) of 5-trimethylsilylbicyclo[2.2.2]oct-2-ene and norbornene possesses good film-forming properties, and its glass transition temperature is 126°C. The gas-transport properties of the copolymer have been studied.
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