Polymerization of N-Methylpyrrole With Bistriazolinediones Via Electrophilic Aromatic Substitution.

Abstract

The reaction of N-methylpyrrole with 4-substituted-1,2,4-triazoline-3,5-diones (4R-TDs), i.e., MeTD (4-methylsubstituted) and PhTD (4-phenyl substituted), at room temperature without use of any catalyst was investigated. The reaction is instantaneous and leads to the formation of a 2:1 adduct in high yield, with substitution occurring at the 2 and 5 positions of the pyrrole moiety via electrophilic aromatic substitution. These compounds were fully characterized by IR,¹³C-NMR,¹H-NMR, and elemental analysis, and were used as model compounds for the polymerization reaction. The reaction of bis-triazolinediones with N-methylpyrrole was carried out in dimethylformamide at room temperature. The reactions are fast and give novel polymer structures. Some structural characterization and physical properties of these new polymers are reported.