Synthesis and characterization of diazonium containing block copolymers via controlled ring opening metathesis polymerization (ROMP) and the subsequent chemical modification

초록

7-Oxanorbornene-5,6-dicarboximide derivatives bearing either an alkyl- or a nitrophenyl group were prepared and these monomers were subjected to the controlled ring opening metathesis polymerization (ROMP). The resulting polymer, poly[N-(n-butyl)-7-oxanorbornene-5,6-carboximide-b-N-(2-(4-nitrobenzoyl)ethyl)-7oxanorbornene-5,6-dicarboxiimide] P(BuONDI-b-NbONDI) (8), showed good molecular weight and narrow polydispersity control (PDI < 1.1). The alkene and the nitrophenyl groups in the block copolymer were selectively reduced using tosyl hydrazide and ammonium sulfide, respectively. The resulting aryl amines in the block polymer were then oxidized to the corresponding diazonium salts by treatment with nitrosyl tetrafluoroborate. The presence of the diazonium groups was verified by IR and cyclic voltammetry (CV), and also by several chemical reactions which are unique for diazonium salts.

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