Synthesis and properties of novel organosoluble and light-colored poly(ester-amide)s and poly(ester-imide)s with triptycene moiety

Abstract

Two series of new triptycene-containing poly(ester-amide)s and poly(ester-imide)s were prepared from 1,4-bis(3-aminobenzoyloxy)triptycene with various aromatic dicarboxylic acids and dianhydrides, respectively. The synthesis of the poly(ester-amide)s was achieved by the phosphorylation polyamidation reaction by means of triphenyl phosphite and pyridine, and the synthesis of the poly(ester-imide)s included ring-opening polyaddition to give poly(amic acid)s followed by thermal imidization and chemical imidization to polyimides. All the poly(ester-amide)s and most of the poly(ester-imide)s presented good solubility in many organic solvents and could be solution-cast into transparent and flexible films. These poly(ester-amide)s and poly(ester-imide)s displayed discernible glass-transition temperatures (Tgs) between 242 and 298 °C in the DSC traces and showed moderate thermal stability with 10 wt% loss temperatures above 464 °C in nitrogen or air. These highly optically transparent polymer films possess an ultraviolet-visible absorption cut-off wavelength (λ0) down to 344 nm. 1,4-Bis(4-aminobenzoyloxy)triptycene was also synthesized and used for polymer synthesis; however, less favorable results were obtained.