Synthesis, Structure and Properties of Fused π‐Extended Acridone Derivatives

Benzene‐ and naphthalene‐fused acridone derivatives with hexyl and phenyl groups at the amino position were synthesized and their properties were investigated experimentally and computationally. All the structures of these fused π‐extended acridone derivatives were unambiguously confirmed by single‐crystal X‐ray analysis, which revealed the presence of face‐to‐face π–π stackings along the acridone moiety and the intermolecular hydrogen bond‐directed molecular packings of the phenyl‐substituted acridone derivatives in the crystals. Moreover, the dimerization of linearly fused acridone derivative was observed after storing the crystals over months. The benzene ring at the turning point of the angularly fused acridone derivatives contained relatively longer and shorter C–C bonds, which affected the molecular conjugation, as confirmed by the results of photophysical characterization and the study of the aromaticity. Mobility calculations based on the molecular packings in the single crystals showed that the linearly fused acridone derivatives bearing better electron and hole mobilities are good candidates of organic functional materials.