Propeller-Shaped Aluminum Complexes with an Azaperylene Core in the Ligands

Abstract

Tris(8-hydroxyquinoline) aluminum(III) (Alq3) and its derivatives, characterized by a propeller-shaped three-dimensionally π-conjugated structure, have been intensively studied in the few past decades on account of their potential utility in optoelectronic applications. Reported herein are the synthesis and properties of π-extended Alq3 complexes that contain an azaperylene core in each ligand. Intramolecular palladium-catalyzed direct C−H arylations or base-promoted arylations were employed to prepare these large Alq3 analogues. A single-crystal X-ray diffraction analysis of one of the obtained Al complexes revealed a unique three-dimensional packing structure within the crystal, i.e., a honeycomb packing along the ab-plane and columnar π-stacks along the c-axis. An Alq3 analogue with azaperylene-dicarboximide ligands exhibited deep blue color in solution with an intense absorption band that extended to 780 nm (λmax = 634 nm; ε = 58,000 M−1 cm−1).

Keywords

• Alq₃
• 8-hydoxyquinoline
• annulation
• direct C–H arylation
• perylene
• PAH