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Open AccessCommunication

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

1
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
2
Graduate School of Engineering, Osaka Institute of Technology, 5-16-1 Omiya, Asahi-ku, Osaka 535-8585, Japan
3
Department of Applied Chemistry, Faculty of Engineering, Osaka Institute of Technology, 5-16-1 Omiya, Asahi-ku, Osaka 535-8585, Japan
4
JST-PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
5
Graduate School of Natural Sciences, Nagoya City University, Yamanohata 1, Mizuho-cho, Mizuho-ku, Nagoya, Aichi 467-8501, Japan
*
Authors to whom correspondence should be addressed.
Inorganics 2019, 7(9), 109; https://doi.org/10.3390/inorganics7090109
Received: 31 July 2019 / Revised: 20 August 2019 / Accepted: 30 August 2019 / Published: 3 September 2019
(This article belongs to the Special Issue Organoaluminum Compounds)
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). View Full-Text
Keywords: Alq3; 8-hydoxyquinoline; annulation; direct C–H arylation; perylene; PAH Alq3; 8-hydoxyquinoline; annulation; direct C–H arylation; perylene; PAH
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MDPI and ACS Style

Tsukao, M.; Hashikawa, Y.; Toyama, N.; Muraoka, M.; Murata, M.; Sasamori, T.; Wakamiya, A.; Murata, Y. Propeller-Shaped Aluminum Complexes with an Azaperylene Core in the Ligands. Inorganics 2019, 7, 109.

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