Benzo[<i>h</i>]quinolin-10-yl-<i>N</i> Iridium(III) Complexes

Nonoyama, Matsuo

doi:10.1246/bcsj.47.767

Cited by 752 publications

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“…The mesppy and dFmesppy C^N ligands were each prepared in high yield via Suzuki-Miyaura 11 palladium-catalysed cross-coupling reactions. The bulky mesityl substituent was incorporated at the 4-position of the pyridine ring of ppy and dFppy C^N ligands as mesityl substitution had been previously shown by Bryce and co-workers 12 15 The qpy ligand was prepared in low yield following an oxidative Pd-catalyzed coupling reaction of 4,4'-bipyridine. 16 Complexes 1 and 2 were isolated through cleavage of D1 and D2 with qpy, whereas complex 3 was prepared through cleavage of D1 with dtbubpy.…”

Section: Synthesismentioning

confidence: 99%

Exploring the self-assembly and energy transfer of dynamic supramolecular iridium-porphyrin systems

et al. 2016

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Section: Synthesismentioning

confidence: 99%

Exploring the self-assembly and energy transfer of dynamic supramolecular iridium-porphyrin systems

et al. 2016

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“…2,8,9 Cyclometalated Ir(III) complexes feature metal-ligand-based luminescent properties and high energy non-emissive metal-centered (MC) states, which enables broad color tuning through structural variation. 8 Cyclometalated diiridium complexes are frequently encountered in the form of μ-dichloro-bridged dimers, which were first reported in 1974 by Nonoyama 10 and are usually synthesized according to Watts' procedure. 11 Such complexes have found widespread use as precursors to cyclometalated heteroleptic and homoleptic monoiridium complexes.…”

Section: Introductionmentioning

confidence: 99%

“…, 2-(2-fluoro-4-methoxyphenyl)pyridine (10) 66 and N,N'-bis(4-tertbutylphenylbenzoyl)hydrazide (11) 72 were all synthesized according to literature procedures. All solvents used were of analytical reagent grade or higher.…”

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confidence: 99%

Synthesis, Diastereomer Separation, and Optoelectronic and Structural Properties of Dinuclear Cyclometalated Iridium(III) Complexes with Bridging Diarylhydrazide Ligands

et al. 2017

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(2017) 'Synthesis, diastereomer separation, and optoelectronic and structural properties of dinuclear cyclometalated iridium(III) complexes with bridging diarylhydrazide ligands. ', Organometallics., 36 (5). pp. 981-993.Further information on publisher's website:https://doi.org/10.1021/acs.organomet.6b00887Publisher's copyright statement:This document is the Accepted Manuscript version of a Published Work that appeared in nal form in Organometallics, copyright c 2017 American Chemical Society after peer review and technical editing by the publisher. To access the nal edited and published work see https://doi.org/10.1021/acs.organomet.6b00887. Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. ABSTRACT: A series of diiridium complexes 13-16 bridged by diarylhydrazine ligands and cyclometalated by phenylpyridine or phenylpyrazole ligands was synthesized. In all cases the ɅΔ meso and ɅɅ/ΔΔ rac diastereomers were separated and characterized by single-crystal X-ray diffraction, revealing intramolecular - stacking between arenes of the bridging and cyclometalating ligands. Density functional theory (DFT) calculations show that in general the HOMOs are mainly localized on the iridium centers, the cyclometalating phenyl moieties and the central hydrazide components of the bridging ligands, while the LUMOs are primarily localized on the N-heterocycles (pyridine or pyrazole) of the cyclometalating ligands. This series of complexes, especially with the separated diastereomers, provides an ideal opportunity to study the effects of subtle structural changes on the optoelectronic properties of diiridium systems: significant differences are observed between the rac and meso isomers in some cases. A cyclic voltammetric study of the electrochemical properties of the eight complexes reveals strong intramolecular interactions between the iridium centers. The photophysical properties are reported in solution, and in rigid poly(methyl methacrylate) (PMMA) or 2-methyltetrahydrofuran (2-MeTHF) (at 77 K) matrices where some of the complexes are strongly emissive in the turquoise and green regions (Φ PL 42-68 ±10%) due to matrix-induced restricted intramolecular motion (RIM).

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“…The cyclometallated iridium(III) μ-chloro bridged dimer [(bt) 2 Ir(μ-Cl)] 2 was prepared as described by Nonoyama with modification. 7 Briefly, IrCl 3 ·3H 2 O (0.71 g, 2 mmol) and 2-phenylbenzothiazole (1.27 g, 6 mmol) were dissolved in a mixture of 2-ethoxyethanol/water (24 mL; 3:1 v/v) and heated at 125°C for 24 h. The reaction mixture was cooled to room temperature and the precipitate collected. The dimer product so obtained was washed with ethanol and hexane, and dried in vacuum (0.88 g, 68%).…”

Section: Methodsmentioning

confidence: 99%

Photophysical Properties of Highly Efficient Blue-Green Emitting Cationic Iridium (III) Complexes Containing Two 2-Phenylbenzothiazole Ligands and One Diphosphine Ligand

Yun¹,

Song²,

Kim³

et al. 2014

Bulletin of the Korean Chemical Society

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Two novel phosphorescent heteroleptic cationic Ir(III) complexes, Ir(bt) 2 (dmpe) (Ir1) and Ir (bt) 2 (dppe) (Ir2), where bt is 2-phenylbenzothiazole, dmpe is 1,2-bis(dimethylphosphino)ethane, and dppe is 1,2-bis(diphenylphosphino)ethane, were designed and synthesized. Their photophysical and electrochemical properties and the X-ray structure of the Ir1 complex were investigated. The prepared Ir(III) complexes exhibited blue-green emissions at 503-538 nm with vibronic fine structures in dichloromethane solution and PMMA film, implying that the lowest excited states are dominated by ligand-based 3 π-π* transitions. The π-acceptor ability of the diphosphine ancillary ligand leads to blue-shift emission. The room temperature photoluminescent quantum yields (PLQYs) of Ir1 and Ir2 were 52% and 45%, respectively, in dichloromethane solution. These high PLQYs resulted from steric hindrances by the bulky cationic iridium complexes. The crystal structure of Ir1 was determined by X-ray crystallography, which revealed that central iridium adopted a distorted octahedral structure coordinated with two bt ligands (N^C) and one dmpe ligand (P^P) showing cis C-C and trans N-N dispositions. The bent nature of the dmpe ligand resulted in a relatively wide bite angle of 83.83 o of P-Ir-P.

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Benzo[h]quinolin-10-yl-N Iridium(III) Complexes

Abstract: Benzo[h]quinoline(bhqH) is metallated with iridium(III) to give [Ir(bhq)2Cl]2 in which bhq is coordinated at 1-N and 10-C atoms. This complex reacts with a ligand(L) such as tri-n-butylphosphine and diethylsulfide to yield [Ir(bhq)2ClL].

Cited by 752 publications

References 1 publication

Exploring the self-assembly and energy transfer of dynamic supramolecular iridium-porphyrin systems

Exploring the self-assembly and energy transfer of dynamic supramolecular iridium-porphyrin systems

Synthesis, Diastereomer Separation, and Optoelectronic and Structural Properties of Dinuclear Cyclometalated Iridium(III) Complexes with Bridging Diarylhydrazide Ligands

Photophysical Properties of Highly Efficient Blue-Green Emitting Cationic Iridium (III) Complexes Containing Two 2-Phenylbenzothiazole Ligands and One Diphosphine Ligand

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