Poly[N-(2-chloroprop-2-en-1-yl)aniline]s: synthesis, polymer analogous reaction, and physicochemical properties

A series of new soluble N-substituted poly(β-haloallylaniline)s, namely poly[N-(2-chloroprop-2-en-1-yl)aniline] (NPC), poly[N-(2-chloroprop-2-en-1-yl)-2-methylaniline] (NPT) and poly[N-(2-chloroprop-2-en-1-yl)-2-methoxyaniline] (NPA), were synthesized by oxidative polymerization in 1 M HCl medium using (NH4)2S2O8 as the oxidant. Based on these polymers and polyphosphoric acid, various functionalized polyindoles of a new type were obtained in high yields. All the polymers obtained were characterized by 1H and 13C NMR, IR and UV-spectroscopy, elemental analysis, scanning electron microscopy (SEM), and thermal gravimetric analysis (TGA). The optical properties were studied, and the indole polymers were found to exhibit photoconductivity. Comparative analysis of spectral data and physicochemical properties indicates that intramolecular cyclization of the polyaniline derivatives occurs successfully.