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η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes

AuthorsEsteruelas, Miguel A. ; Gómez-Bautista, Daniel ; López, Ana M. ; Oñate, Enrique ; Tsai, Jui-Yi; Xia, Chuanjun
KeywordsC−H activation
Heteroleptic complexes
Tridentate ligands
Arene ligands
Issue Date2017
CitationChemistry - A European Journal 23(62): 15729-15737 (2017)
AbstractMolecular phosphorescent heteroleptic bis-tridentate iridium(III) emitters have been prepared via η1-arene intermediates. In the presence of 4.0 mol of AgOTf, the complex [(IrCl{κ3-N,C,N-(pyC6HMe2py)})(μ-Cl)]2 (1; pyC6H2Me2py=1,3-di(2-pyridyl)-4,6-dimethylbenzene) reacted with 9-(6-phenylpyridin-2-yl)-9H-carbazole (PhpyCzH) and 2-phenoxy-6-phenylpyridine (PhpyOPh) to give [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyCzH)}]OTf (2) and [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyOPh)}]OTf (3). The X-ray diffraction structures of 2 and 3 reveal that the carbazolyl and phenoxy substituents of the C,N,C′ ligand coordinate to the metal center to form an η1-arene π bond. Treatment of 2 and 3 with KOtBu led to the deprotonation of the coordinated carbon atom of the η1-arene group to afford the molecular phosphorescent [5t+4t′] heteroleptic iridium(III) complexes [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyCz)}] (4) and [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyOC6H4)}] (5). These complexes are green emitters that display short lifetimes and high quantum yields of 0.73 (4) and 0.87 (5) in the solid state.
Publisher version (URL)https://doi.org/10.1002/chem.201703252
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