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Issue 23, 2012
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Exploring synthetic pathways to cationic heteroleptic cyclometalated iridium complexes derived from dipyridylketone

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Abstract

Reactions between 2,2′-dipyridylketone (L1) and different amines gave a series of iminic ligands, and their chemical reductions produced the related amines. The organic ligands were employed in the syntheses of the corresponding new phosphorescent six-member ring bis-cyclometalated heteroleptic iridium(III) complexes of general formula [Ir(ppy)2(L)]+ (ppy = 2-phenylpyridine), namely IrLn. The metal complexes containing N-(dipyridin-2-ylmethylene)butan-1-amine (IrL2), N-(dipyridin-2-ylmethyl)butan-1-amine (IrL5), N-(dipyridin-2-ylmethyl)butane-1,4-diamine with amino groups protected by Boc (IrL6-Boc) and TFA (IrL6-TFA), and N-(dipyridin-2-ylmethyl)-N-methylbutan-1-amine (IrL8) were characterized and their electronic and spectroscopic properties interpreted by DFT calculations. Organoiridium complexes containing amines and imines were found to have high and low photoemission quantum yields, respectively, and their features rationalized by quantum mechanic calculations. Some of these complexes show reasonable quantum yields (up to 13%), long lifetime (up to 2.3 μs) and high stability. Complementary and alternative synthetic pathways to get cationic heteroleptic cyclometalated Ir complexes bearing a tethered primary amino group have been explored with the aim to obtain organometallic phosphorescent derivatives suitable for surface functionalization.

Graphical abstract: Exploring synthetic pathways to cationic heteroleptic cyclometalated iridium complexes derived from dipyridylketone

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Publication details

The article was received on 20 Feb 2012, accepted on 04 Apr 2012 and first published on 04 Apr 2012


Article type: Paper
DOI: 10.1039/C2DT30399J
Citation: Dalton Trans., 2012,41, 7098-7108
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    Exploring synthetic pathways to cationic heteroleptic cyclometalated iridium complexes derived from dipyridylketone

    G. Volpi, C. Garino and C. Nervi, Dalton Trans., 2012, 41, 7098
    DOI: 10.1039/C2DT30399J

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