Cruciform Alkynylated Anthanthrene Derivatives: A Structure-Properties Relationship Case Study

An efficient and versatile synthetic strategy toward cruciform anthanthrene compounds using Sonogashira couplings steps was developed. Acetylenic linkers were used to effectively extend the pi-conjugation of polycyclic anthanthrone and anthanthrene compounds and tune their optoelectronic properties. Structure-property relationships supported by DFT calculations indicated more effective pi-conjugation along the 6,12 axis than along the 4,10 axis. These molecules displayed strong J-aggregation both in solution and in the solid state and proved to be highly photostable with reversible redox processes, which are properties of interest in materials sciences.