First cyclometalated iridium(III) complex containing methyl 2-amino-2-deoxy-β-d-glucopyranoside as N,O-chelate

The syntheses of bis-cyclometalated complexes containing R-3-amino-1,2-propanediolato ligands of the type [M(ptpy)2(R-3-amino-1,2-propanediolato)] (M = Rh, 1; M = Ir, 2; ptpy = 2-(p-tolyl)pyridinato) are reported. They were prepared from [{M(μ-Cl)(ptpy)2}2] (M = Rh, Ir) by the reaction of the corresponding aminodiol with sodium methanolate as the base. Furthermore the related reaction of [{Ir(μ-Cl)(ptpy)2}2] with the sugar derivative methyl 2-amino-2-deoxy-β-d-glucopyranoside hydrochloride in the presence of the base is described. A single-crystal X-ray diffraction study confirmed the expected N,O chelate formation and the 1:1 stoichiometry in the formed complex [Ir(ptpy)2(amino sugar-N,O)] (3). Compound 3 crystallized from methanol in the space group P21 and two diastereoisomers ΔIr, RC and ΛIr, RC were found. The absorption and emission spectra were recorded exhibiting all compounds as green emitters.

The synthesis of bis-cyclometalated complexes containing N,O chelating amino alcoholato ligands of the type [M(ptpy)2(N^O)] (N^O = R-3-amino-1,2-propanediolato, M = Rh, 1; M = Ir, 2; N^O = methyl 2-amino-2-deoxy-β-d-glucopyranoside, M = Ir (3); ptpy = 2-(p-tolyl)pyridinato) are reported. A single-crystal X-ray diffraction study confirmed the expected N,O chelate formation and the 1:1 stoichiometry in the formed complex [Ir(ptpy)2(amino sugar-N,O)] (3). The absorption and emission spectra were recorded exhibiting all compounds as green emitters.Figure optionsDownload as PowerPoint slideHighlights
► Syntheses of cyclometalated Rh, Ir complexes with aminodiol or amino sugar ligands.
► A single-crystal X-ray study confirmed the N,O chelate in the Ir amino sugar complex.
► The absorption and emission spectra exhibit all compounds as green emitters.