Electrochemical route to xylylene polymers and copolymers via cathodically generated quinodimethanes: preparative and structural aspects

Abstract

Electrochemical reductive elimination of bis(α-bromoalkyl)arenes gives quinodimethane intermediates that polymerize, mostly in high yield, to linear polymers of the poly(p-xylylene) type. At a stirred mercury cathode reaction proceeds to completion and the polymers precipitate. A considerable variety of structural variation in the precursors is tolerated. Co-electrolysis of different precursors gives copolymers. In some cases organo-sole fractions are formed. Key structural features of the polymers and copolymers are obtained by NMR spectroscopy [¹H and ¹³C (solution and solid-state)] and by direct pyrolysis mass spectrometry. The high reactivity of the p-quinodimethanes is evident from the observed random polymerization and co-polymerization.