One-pot chemical synthesis of poly(pyrrylmethenequinones) from pyrrol and tereph taldicarboxaldehyde

Summary form only given. A simple chemical synthesis of poly(pyrrylmethenequinonoids), represented by the formulas: and for completely oxidized (A), partly protonated (B) and totally deprotonated (C) forms, respectively, is reported. The polymer products characterization by EA, UV/VIS/NIR, FTIR, NIR-FT-Raman, ESR, NMR, TGA and DSC methods is discussed. Mechanistic and preparative aspects of the polycondensation reaction between pyrrol and terephtal-dicarboxaldehyde in oxidizing media are discussed in terms of improvement of yield of the linear conjugated polymer products due to reduction of porphyrinoid and/or 3D-cross-linked structures formation, which is possible through the participation of, e.g., meso-tetrakis[4-(formyl)phenyl]-porphyrinogens and/or poly(pyrrylmethanes). Properties of the new conjugated copolymers are reported and compared to those of known low-band-gap heteroaromatic polymers and copolymers.