Synthesis and characterization of novel polybenzimidazoles containing 4-phenyl phthalazinone moiety

A novel series of homo- and copoly(phthalazinone benzimidazole)s were synthesized from various stoichiometric mixtures of 4-(4-(4-(4-carboxyphenoxy)phenyl)-1-oxophthalazin-2(1H)-yl)benzoic acid (CPPBC) and isophthalic acid (IPA) with 3,3′-diaminobenzidine (DAB) by solution polycondensation in polyphosphoric acid (PPA). The structures of the obtained polymers were characterized by FT-IR and 1H NMR. The obtained polybenzimidazoles were found to be soluble in aprotic polar solvents such as N-methyl-2-pyrolidinone (NMP), N,N-dimethylacetamide (DMAc), dimethyl sulfoxide (DMSO) and m-cresol, without the addition of inorganic salts. The inherent viscosities of the polybenzimidazoles were in the range of 1.10–2.05 dL/g. All of the polymers show amorphous nature as evaluated by WAXD. These polymers have high glass transition temperatures (Tgs) in the range of 398–408 °C. Thermogravimetric analysis exhibit that these polybenzimidazoles containing 4-phenyl phthalazinone moiety have excellent thermal stability with the temperatures for 5% and 10% weight loss of the polymers ranging from 516 to 594 °C and 560 to 672 °C, respectively.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A novel series of polybenzimidazoles containing non-coplanar 4-phenyl phthalazinone moiety have been synthesized. ► The inherent viscosities of the polybenzimidazoles were in the range of 1.10 to 2.05 dL/g. ► They have good solubility in polar aprotic solvents. ► They exhibit excellent thermal stability and high glass transition temperatures.