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1.
Chemistry ; 23(5): 1118-1128, 2017 Jan 23.
Article in English | MEDLINE | ID: mdl-27859741

ABSTRACT

Cyclometalated thiazol-2-ylidene platinum(II) complexes based on the N-phenyl-4,5-dimethyl-1,3-thiazol-2-ylidene N-heterocyclic carbene (NHC) ligand and seven different ß-diketonate ligands have been synthesised and investigated for their structural and photophysical properties. The complexes were synthesised in a one-pot procedure starting with the in situ formation of the corresponding silver(I) carbene and transmetalation to platinum, followed by the reaction with the respective ß-diketonate under basic conditions. All the compounds were fully characterised by standard techniques, including 195 Pt NMR spectroscopy. Three solid-state structures revealed quite different aggregation behaviour depending on the ß-diketonate architecture. The reported complexes showed strong phosphorescence at room temperature in amorphous poly(methyl methacrylate) films. The emission wavelengths (ca. 510 nm) were found to be independent of the ß-diketonate ligand, but the electronically diverse ß-diketonates strongly influence the observed quantum yields (QY) and decay lifetimes. The results of theoretical studies employing density functional theory (DFT) methods support the conclusion of a metal-to-ligand charge transfer (3 MLCT) as the main emission process, in accordance with the reported photophysical properties. Standard organic light-emitting diodes (OLEDs) prepared with unoptimised matrix materials using one of the complexes showed values of 12.3 % external quantum yield, 24.0 lm W-1 luminous efficacy and 37.8 cd A-1 current efficiency at 300 cd m-2 .

2.
Angew Chem Int Ed Engl ; 55(51): 15779-15782, 2016 12 19.
Article in English | MEDLINE | ID: mdl-27860097

ABSTRACT

Binuclear C^C* cyclometalated NHC platinum(II) compounds with bridging amidinate ligands were synthesized to evaluate their photophysical properties. Their three-dimensional structures were determined by a combination of 2D NMR experiments, mass spectrometry, DFT calculations, and solid-state structure analysis. The bridging amidinate ligands enforce short distances between the platinum centers of the two cyclometalated structures, which gives rise to extraordinary photophysical properties.

3.
Chemistry ; 22(29): 9914-8, 2016 Jul 11.
Article in English | MEDLINE | ID: mdl-27294887

ABSTRACT

The synthesis and characterization of eight unprecedented phosphorescent C^C* cyclometalated mesoionic aryl-1,2,3-triazolylidene platinum(II) complexes with different ß-diketonate ligands are reported. All compounds proved to be strongly emissive at room temperature in poly(methyl methacrylate) films with an emitter concentration of 2 wt %. The observed photoluminescence properties were strongly dependent on the substitution on the aryl system and the ß-diketonate ligand. Compared to acetylacetonate, the ß-diketonates with aromatic substituents (mesityl and duryl) were found to significantly enhance the quantum yield while simultaneously reducing the emission lifetimes. Characterization was carried out by standard techniques, as well as solid-state structure determination, which confirmed the binding mode of the carbene ligand. DFT calculations, carried out to predict the emission wavelength with maximum intensity, were in excellent agreement with the (later) obtained experimental data.

4.
Chemistry ; 21(37): 12881-4, 2015 Sep 07.
Article in English | MEDLINE | ID: mdl-26215315

ABSTRACT

Two C^C* cyclometalated platinum(II) N-heterocyclic carbene (NHC) complexes with the general formula [(C^C*)Pt(O^O)] (C^C*=1-dibenzofuranyl-3-methylbenzimidazolylidene; O^O=dimesitoylmethane) have been synthesized and extensively characterized, including solid-state structure determination, (195) Pt NMR spectroscopy, and 2D NMR (COSY, HSQC, HMBC, NOESY) spectroscopy to elucidate the impact of their structural differences. The two regioisomers differ in the way the dibenzofuranyl (DBF) moiety of the NHC ligand is bound to the metal center, which induces significant changes in their physicochemical properties, especially on the decay time of the excited state. Quantum yields of over 80 % and blue emission colors were measured.

5.
Inorg Chem ; 53(12): 6346-56, 2014 Jun 16.
Article in English | MEDLINE | ID: mdl-24866934

ABSTRACT

Cyclometalated (C^C*) platinum(II) N-heterocyclic carbene (NHC) complexes are emerging as a new class of phosphorescent emitters for the application in organic light-emitting devices (OLEDs). We present the synthesis of six new complexes of this class to investigate the influence of extended π systems. Therefore, six different NHC ligands with a varying number of additional phenyl substituents were used in combination with the monoanionic acetylacetonate (acac) ligand to obtain complexes of the general formula [(NHC)Pt(II)(acac)]. The complexes were fully characterized by standard techniques and advanced spectroscopic methods ((195)Pt NMR). For all complexes the solid-state structure determination revealed a square-planar coordination of the platinum atom. Absorption and emission spectra were measured in thin amorphous poly(methyl methacrylate) films at room temperature. Four compounds emit in the blue-green region of the visible spectrum with quantum yields of up to 81%.

6.
Dalton Trans ; 43(8): 3297-305, 2014 Feb 28.
Article in English | MEDLINE | ID: mdl-24362536

ABSTRACT

Since C^C* cyclometalated Pt(II) complexes with N-heterocyclic carbene (NHC) ligands have been identified as potential emitter materials in organic light-emitting devices (OLEDs), very promising results regarding quantum yields, colour and stability have been presented. Herein, we report on four nitrile substituted complexes with a chelating NHC ligand (1-(4-cyanophenyl)-3-isopropyl-1H-benzo[d]imidazole or 4-(tert-butyl)-1-(4-cyanophenyl)-3-methyl-1H-imidazole) and a bidentate monoanionic auxiliary ligand (acetylacetone or dimesitoylmethane). The complexes have been fully characterized including extensive 2D NMR studies (COSY, HSQC, HMBC, NOESY, (195)Pt NMR), three of them also by solid-state structures. Photophysical measurements in amorphous PMMA films and pure emitter films at room temperature reveal the impact of the mesityl groups in the auxiliary ligand, which led to a significant increase of the quantum yield, while the decay lifetimes decreased. The electron withdrawing nitrile groups shift the emission towards blue colour coordinates.

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