1,6-Naphthodione-based monomers and polymers

Novel 1,6-naphthodione monomers and π-conjugated polymers were synthesized and characterized. Monomeric 1,6-naphthodifuranones and -dipyrrolidones exhibit purple to blue colors with high extinction coefficients up to 4.6 × 104 L mol−1 cm−1. As shown by X-ray crystal structure analysis, the naphthodipyrrolidone core is fully planar. 1,6-Naphthodione-based polymers exhibit low band gaps (1.20–1.41 eV) and broad absorption bands (400–1000 nm). Due to their interesting electronic and optical properties, and their planar structure, naphthodione-based monomers are promising building blocks for novel π-conjugated polymers with potential applications in optoelectronics.