Homogeneous catalysis in the preparation of new carboximide-based thermoplastic polymers

The ring opening metathesis polymerization (ROMP) of norbornene dicarboximide derivatives 3(a–c) bearing halo-substituted phenyl groups was carried out with well-defined organometallic catalyst (PCy3)2(Cl)2RuCHPh. This catalyst is highly active for the polymerization of norbornene dicarboximide derivatives. Exo-N-4-chlorophenyl-norbornene-5,6-dicarboximide (ClPhNDI, 3a), exo-N-4-bromophenyl-norbornene-5,6-dicarboximide (BrPhNDI, 3b), exo-N-4-iodophenyl-norbornene-5,6-dicarboximide (IPhNDI, 3c) monomers gave high molecular weight thermoplastic polymers in high yields (77–96%). All of the prepared polymers were soluble in common organic solvents at room temperature and gave similar IR and NMR spectra. Their glass transition temperatures were detected at temperatures over 187 °C. The surface properties of ROMP polymers were investigated by SEM.

Graphical abstractThe applicability of organometallic catalyst (PCy3)2(Cl)2RuCHPh as initiator in the ring opening metathesis polymerization (ROMP) of norbornene dicarboximide derivatives bearing halo-substituted phenyl groups has been investigated. The synthesis and polymerization of exo-N-4-chlorophenyl-norbornene-5,6-dicarboximide (ClPhNDI), exo-N-4-bromophenyl-norbornene-5,6-dicarboximide (BrPhNDI) and exo-N-4-iodophenyl-norbornene-5,6-dicarboximide (IPhNDI) are reported. All of the prepared polymers were soluble in common organic solvents.Figure optionsDownload full-size imageDownload high-quality image (65 K)Download as PowerPoint slide