Emission Tuning of Ir(N<sup>∧</sup>C)<sub>2</sub>(pic)-Based Complexes via Torsional Twisting of Picolinate Substituents

Davidson, Ross J.; Hsu, Yu-Ting; Yufit, Dmitry S.; Beeby, Andrew

doi:10.1021/acs.organomet.8b00194

Cited by 9 publications

(2 citation statements)

References 24 publications

(34 reference statements)

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“…The Freixa group has used this procedure to append azobenzene moieties to the phenyl group, in order to study the effect that the extended conjugation and substitution pattern has on the photochromic behavior of the azobenzene-appended 2-phenylpyridine ligands . The postfunctionalization of the 3b′ and 4b ligands of [3b + 3b + 3b′] and [3b + 3b + 4b] + iridium(III) complexes has been also reported by several research groups . In addition, Williams and co-workers have constructed multimetallic broad-band light emitters, by means of the assembly of mononuclear bis-terpyridyl complexes with extended conjugation .…”

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confidence: 99%

Suzuki–Miyaura Cross-Coupling Reactions for Increasing the Efficiency of Tris-Heteroleptic Iridium(III) Emitters

et al. 2019

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The complex Ir(acac){κ2-C,N-[C6BrH3-py]}{κ2-C,N-[C6H4-py]} (2) is a green emitter, which displays short lifetimes (0.9–4.9 μs) and quantum yields of 0.32 in poly(methyl methacrylate) films at 5 wt % and 0.41 in 2-methyltetrahydrofuran at room temperature. Its Pd(OAc)2/4 PPh3-catalyzed cross-coupling reactions with RB(OH)2 afford Ir(acac){κ2-C,N-[C6RH3-py]}{κ2-C,N-[C6H4-py]} (R = Me (3), Ph (4)), which show almost identical emissions with quantum yields in the range 0.98–0.82.

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confidence: 99%

Suzuki–Miyaura Cross-Coupling Reactions for Increasing the Efficiency of Tris-Heteroleptic Iridium(III) Emitters

et al. 2019

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“…The synthesis of iridium(III) emitters generally involves ligand displacement and addition reactions, whereas the generation of structures by means of organometallic transformations on the metal coordination sphere or selective postfunctionalization of a coordinated ligand via catalysis , has been rarely used. In agreement with the general protocol, the [3b+3b+3b′] compounds are usually prepared by reaction of the corresponding dimers [Ir(μ-Cl)(3b) 2 ] 2 with a β-diketonate salt .…”

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confidence: 99%

Insertion of Unsaturated C–C Bonds into the O–H Bond of an Iridium(III)-Hydroxo Complex: Formation of Phosphorescent Emitters with an Asymmetrical β-Diketonate Ligand

et al. 2020

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Structural Analysis of Complexes 4, 5, and 7 S3 Computational Details S5 Energies of Optimized Structures S5 UV-vis Spectra of Complexes 4-7 (Observed and Calculated) S9 Analysis of Computed UV/Vis Data for 4-7 S10 Cyclic Voltammograms of Complexes 4-7 S15 Theoretical Analysis of Molecular Orbitals of Complexes 4-7 S16 Normalized Excitation and Emission Spectra of Complexes 4-7 S25 NMR Spectra of Complexes 2-7 S29 References S42 S3 Experimental Section: General Information. All reactions were carried out with rigorous exclusion of air using Schlenk-tube techniques. Solvents were dried by the usual procedures and distilled under argon prior to use or obtained oxygen-and water-free from an MBraun solvent purification apparatus. C, H, and N analyses were carried out in a Perkin-Elmer 2400B SeriesII-Analyzer. High-resolution (HRMS) were acquired using a MicroTOF-Q hybrid quadrupole time-of-flight spectrometer (Bruker Daltonics, Bremen, Germany). MALDI-TOF mass spectra were acquired using a Bruker Autoflex III, MALDI-TOF/TOF equipped with a DCTB matrix. IR spectra were measured using a PerkinElmer Spectrum 100 FT-IR spectrometer, equipped with an ATR accessory, as pure solids. 1 H and 13 C{ 1 H} NMR spectra were recorded on a Bruker Avance 300 or 400 MHz instrument. Chemical shifts (expressed in parts per million) are referenced to residual solvent peaks. Coupling constants J are given in hertz. UV-visible spectra were registered on an Evolution 600 spectrophotomer. Steady-state photoluminescence spectra were recorded on a Jobin-Yvon Horiba Fluorolog FL-3-11 spectrofluorimeter. Lifetimes were measured using an IBH 5000F coaxial nanosecond flash lamp. Quantum yields were measured using the Hamamatsu Absolute PL Quantum Yield Measurement System C11347-11. Cyclic voltammetry measurements were performed using a Voltalab PST050 potentiostat with Pt wire as working electrode, Pt wire as counter electrode, and saturated calomel (SCE) as reference electrode. The experiments were carried out under argon in dichloromethane or acetonitrile solutions (10-3 M), with Bu 4 NPF 6 as supporting electrolyte (0.1 M). Scan rate was 100 mV s-1. The potentials were referenced to the ferrocene/ferrocenium (Fc/Fc +) couple. Preparation of [Ir(μ-Cl)(κ 2-C,N-C 6 H 4-isoqui) 2 (1). A suspension of [Ir(μ-Cl)(η 2-COE) 2 ] 2 (500 mg, 0.56 mmol) in 10 mL of 2-ethoxyethanol was treated with 1phenylisoquinoline (470 mg, 2.30 mmol) and the mixture was refluxed for 12 h. The resulting suspension was filtered and the red solid was washed with diethyl ether (3 x 10 mL). Yield: 620 mg (87%). 1 H NMR (300 MHz, CD 2 Cl 2 , 298 K): δ 9.00 (m, 4H), 8.20 (d,

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Palladium‐Catalyzed C−H Bond Arylation of Cyclometalated Difluorinated 2‐Arylisoquinolinyl Iridium(III) Complexes

Peng

Lin

et al. 2021

Chemistry A European J

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The utility of CÀ H bond functionalization of metalated ligands for the elaboration of aryl-functionalized difluorinated-1-arylisoquinolinyl Ir(III) complexes has been explored.Bis [(3,5-difluorophenyl)isoquinolinyl](2,2,6,6tetramethyl-3,5-heptanedionato) iridium(III) undergoes Pdcatalyzed CÀ H bond arylation with aryl bromides. The reaction regioselectively occurred at the CÀ H bond flanked by the two fluorine atoms of the difluoroaryl unit, and on both cyclometalated ligands. This post-functionalization gives a straightforward access to modified complexes in only one manipulation and allows to introduce thermally sensitive functional groups, such as trifluoromethyl, nitrile, benzoyl, or ester. The X-ray crystallography, photophysical, and electrochemical properties of the diarylated complexes were investigated. Whatever the nature of the incorporated substituted aryl groups is, all obtained complexes emit red phosphorescence (622-632 nm) with similar lifetimes (1.9-2 μs).

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Emission Tuning of Ir(N^∧C)₂(pic)-Based Complexes via Torsional Twisting of Picolinate Substituents

Cited by 9 publications

References 24 publications

Suzuki–Miyaura Cross-Coupling Reactions for Increasing the Efficiency of Tris-Heteroleptic Iridium(III) Emitters

Suzuki–Miyaura Cross-Coupling Reactions for Increasing the Efficiency of Tris-Heteroleptic Iridium(III) Emitters

Insertion of Unsaturated C–C Bonds into the O–H Bond of an Iridium(III)-Hydroxo Complex: Formation of Phosphorescent Emitters with an Asymmetrical β-Diketonate Ligand

Palladium‐Catalyzed C−H Bond Arylation of Cyclometalated Difluorinated 2‐Arylisoquinolinyl Iridium(III) Complexes

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Emission Tuning of Ir(N∧C)2(pic)-Based Complexes via Torsional Twisting of Picolinate Substituents

Cited by 9 publications

References 24 publications

Suzuki–Miyaura Cross-Coupling Reactions for Increasing the Efficiency of Tris-Heteroleptic Iridium(III) Emitters

Suzuki–Miyaura Cross-Coupling Reactions for Increasing the Efficiency of Tris-Heteroleptic Iridium(III) Emitters

Insertion of Unsaturated C–C Bonds into the O–H Bond of an Iridium(III)-Hydroxo Complex: Formation of Phosphorescent Emitters with an Asymmetrical β-Diketonate Ligand

Palladium‐Catalyzed C−H Bond Arylation of Cyclometalated Difluorinated 2‐Arylisoquinolinyl Iridium(III) Complexes

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Emission Tuning of Ir(N^∧C)₂(pic)-Based Complexes via Torsional Twisting of Picolinate Substituents