Abstract: This study reports, for the first time, the synthesis of a heterocyclic pyridazinone monomer (AGPZ) derived from the biobased compound acetosyringone. Theoretical simulations of the phenoxide anions of AGPZ and the previously reported guaiacol-derived monomer 6-(4-hydroxy-3-methoxyphenyl) pyridazin-3(2H)-one (GSPZ) were conducted using Materials Studio. Comparative analysis revealed that the nucleophilic substitution activity of AGPZ is lower than that of GSPZ. Nevertheless, the successful synthesis of an AGPZ model compound confirmed that AGPZ still possesses sufficient nucleophilic substitution reactivity. A series of biobased poly (aryl ether ketone), named as PAFEKKs, was synthesized through ternary copolymerization of AGPZ with the furan-2,5-diylbis((4-fluorophenyl)methanone) (BFBF) and 9,9-bis(4-hydroxyphenyl)fluorene (BHPF). The synthesized PAFEKKs show a glass transition temperature (Tg) in the range of 217~226 °C and a 5% weight loss decomposition temperature (Td,5%) between 419 and 474 °C, demonstrating excellent thermal stability. Furthermore, PAFEKKs exhibit good solubility, readily dissolving in most common organic solvents at room temperature. This copolymerization strategy utilizing biomass-derived monomers offers a molecular design and synthetic route for biobased resins, presenting a promising avenue for the development of sustainable monomers and polymers with diverse structural architectures.

Key words: Biobased polymer materials, Poly(aryl ether ketone)s, Acetosyringone, Molecular structure and Performance