Semiaromatic polyamides are attractive engineering polymers owing to their outstanding thermo-mechanical properties. To expand the scope of semiaromatic polyamides by additional optoelectronic features, one may consider the incorporation of extended pi-conjugated systems based on fused heterocycles into the polymer backbone. Here, we report on the five-step synthesis of a benzofurobenzofuran dicarboxylic acid monomer on the gram-scale starting from commercial precursors along with its structural characterization. Three corresponding polyamides were prepared by solution-phase polycondensation under Yamazaki-Higashi conditions to prove the suitability of this method for the synthesis of semiaromatic polyamides based on fused heterocyclic cores. The polyamides were thermally characterized and investigated with respect to their chemical and supramolecular structures, as well as their optical and electronic properties.