Journal
INORGANICS
Volume 7, Issue 9, Pages -Publisher
MDPI
DOI: 10.3390/inorganics7090109
Keywords
Alq(3); 8-hydoxyquinoline; annulation; direct C-H arylation; perylene; PAH
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Funding
- JSPS KAKENHI [26600025]
- Osaka Institute of Technology
- Grants-in-Aid for Scientific Research [26600025] Funding Source: KAKEN
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Tris(8-hydroxyquinoline) aluminum(III) (Alq(3)) and its derivatives, characterized by a propeller-shaped three-dimensionally pi-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 pi-extended Alq(3) 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 Alq(3) 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 pi-stacks along the c-axis. An Alq(3) analogue with azaperylene-dicarboximide ligands exhibited deep blue color in solution with an intense absorption band that extended to 780 nm (lambda(max) = 634 nm; epsilon = 58,000 M-1 cm(-1)).
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