From virtual screening to synthesis: designing redox-active phthalimides

Phthalimides are versatile heterocycles with potential as redox-active organic molecules for energy storage applications. A key advantage of this class is their accessibility through sustainable synthetic routes based on renewable feedstocks. Biobased phthalimides can be obtained via Diels-Alder cycloaddition followed by aromatization between maleimides and furans sourced from amino acids, cellulose, and chitin1,providing an atom-economical and resource-efficient approach aligned with green chemistry principles. In this work, a combined molecular design2 and synthesis approach was employed to explore the chemical space of phthalimide derivatives. A virtual library of 5,705 compounds was generated and evaluated by DFT calculations, while statistical modeling and clustering revealed structure–property relationships3 guiding the selection of synthetically accessible targets. Four phthalimide derivatives were prepared through Diels– Alder/aromatization reactions and classical methodologies. Electrochemical characterization revealed that one phthalimide exhibited excellent stability over 2,000 redox cycles, highlighting how computational design can accelerate the discovery of high-performance redox-active organic materials.