94928-86-6

Basic information

• Product Name: Tris(2-phenylpyridine)iridium
• Synonyms: TRIS(2-PHENYLPYRIDINE)IRIDIUM;TRIS(2-PHENYLPYRIDINE)IRIDIUM (III);TRIS(2-PHENYLPYRIDINE)IRIDIUM(III) OLED GREEN LIGHT EMITTER ΛPL 512 NM (FILM);Ir(ppy)3;Tris(2-phenylpyridinato)iridium(III) (purified by sublimation);Ir(ppy)3, Iridium, tris[2-(2-pyridinyl-KN)phenyl-KC];Tris[2-phenylpyridinato-C2,N]iridium(III);Tris(2-phenylpyridinato)iridium(III)
• CAS NO: 94928-86-6
• Molecular Formula: C₃₃H₂₄IrN₃
• Molecular Weight: 654.79
• EINECS: 1312995-182-4
• Product Categories: electronic;Electronic Chemicals;Classes of Metal Compounds;Highly Purified Reagents;Ir (Iridium) Compounds;Other Categories;Refined Products by Sublimation;Transition Metal Compounds;olde Materials;oled materials;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials
• Mol File: 94928-86-6.mol

Chemical Properties

• Melting Point: 328°C
• Appearance: yellow/Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive: air sensitive
• CAS DataBase Reference: Tris(2-phenylpyridine)iridium(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(2-phenylpyridine)iridium(94928-86-6)
• EPA Substance Registry System: Tris(2-phenylpyridine)iridium(94928-86-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 94928-86-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Light-Emitting Diodes (OLEDs):
Tris(2-phenylpyridine)iridium is used as a phosphorescent emitter in OLEDs for its high quantum yields and thermal stability, contributing to the efficiency and performance of these devices.
Used in Suzuki Reaction:
Tris(2-phenylpyridine)iridium can be employed as a catalyst in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry for the formation of carbon-carbon bonds.
Used in Photoredox Catalysis:
Tris(2-phenylpyridine)iridium is used as a photoredox catalyst in the preparation of fused-quinoxaline derivatives, difluorinated ketones, and carbazoles, enabling efficient and selective synthetic pathways.
Used in Optogenetics:
Tris(2-phenylpyridine)iridium can be a useful modifier in optogenetic control of behavior of larva expressing ChR2 in Drosophila melanogaster, allowing for the manipulation of neural activity using light.
Used in Cancer Research and Therapy:
Tris(2-phenylpyridine)iridium can be useful in the development of a metal-containing nucleoside that possesses both therapeutic and diagnostic activity against cancer, offering potential applications in cancer treatment and imaging.

Reactions

Photocatalyst for ?-amino C–H arylation of cyano(hetero)arenes by tertiary amines Photocatalyst for trifluoromethylation of alkenes and alkynes Photocatalyst for reduction of alkyl, alkenyl, aryl iodides (a) and intramolecular reductive cyclizations (d) Photocatalyst for organocatalyst assisted direct arylation of allylic sp3 C–H bonds Photocatalyst for the generation multifluorinated biaryls via functionalization of the C?F bond of a perfluoroarene and C?H bond of the other arene in the presence of amines Photocatalyst for visible-light photoredox arylation of thiols with various aryl halides

InChI:InChI=1/3C11H8N.Ir/c3*1-2-6-10(7-3-1)11-8-4-5-9-12-11;/h3*1-6,8-9H;/rC33H24IrN3/c1-4-16-28(25(13-1)31-19-7-10-22-35-31)34(29-17-5-2-14-26(29)32-20-8-11-23-36-32)30-18-6-3-15-27(30)33-21-9-12-24-37-33/h1-24H

Upstream product

• 1008-89-5 2-phenylpyridine 
• 2622-67-5 1,2-diphenyl-1H-benzoimidazole 
• 3297-72-1 1-phenylisoquinoline 
• 156021-08-8 2,5-diphenyl-4-methylpyridine 

Downstream Products

• 562824-28-6 [Ir(N,C'-NC₅H₄-2-C₆H₄-2)₃]⁽¹⁺⁾ 

Relevant articles and documents

Preparation method of mer-Ir(ppy)3

The invention discloses a preparation method of mer-Ir(ppy)3, belongs to the field of organic iridium complex luminescent materials. Particularly, mer-Ir(ppy)3 is prepared by taking iridium acetylacetonate as a precursor and o-dichlorotoluene or diethylene glycol diethyl ether as a solvent, carrying out heating reflux reaction on the precursor and 2-phenylpyridine under the protection of inert gas, conducting cooling, filtering, washing and drying and conducting column purification. According to the method, a solvent with very small solubility to mer-Ir(ppy)3 is selected, and the method has the advantages of simple process, short synthesis time, high purity, high yield and the like, and is suitable for batch preparation.

Emission Intensity Enhancement for Iridium(III) Complex in Dimethyl Sulfoxide under Photoirradiation

We found emission intensity enhancement for fac-Ir(ppy)3 (ppy = 2-(2′-phenyl)pyridine) in aerated dimethyl sulfoxide (DMSO) during photoirradiation for the first time. This phenomenon was concluded to be responsible for the consumption of 3O2 dissolved in DMSO through dimethyl sulfone production by photosensitized reaction using fac-Ir(ppy)3. A 3O2 adduct of DMSO molecule was detected by UV absorption measurement and theoretical calculation. We proposed a mechanism for the emission enhancement reaction including 1,3O2 molecules and 1,3O2-DMSO adducts and validated it through a simulation of emission intensity change using an ordinary differential equation solver.

METHOD FOR THE SYNTHESIS AND ISOLATION OF FACIAL-TRIS-HOMOLEPTIC PHENYLPYRIDINATO IRIDIUM (III) PHOTOCATALYSTS

Methods of synthesizing and isolating facial-tris-homoleptic phenylpyridinato iridium (III) photocatalysts are disclosed. Also disclosed are methods of recovering excess 2- phenylpyridine ligands from said syntheses.

METHOD FOR PRODUCING CYCLOMETALATED IRIDIUM COMPLEX

The present invention provides a method for producing a cyclometalated iridium complex by use of a non-chlorine iridium raw material. The method for producing a cyclometalated iridium complex includes producing a cyclometalated iridium complex by reacting a raw material including an iridium compound with an aromatic heterocyclic bidentate ligand capable of forming an iridium-carbon bond, the raw material being non-halogenated iridium having a conjugated base of a strong acid as a ligand. Here, the non-halogenated iridium is preferably one containing a conjugated base of a strong acid having a pKa of 3 or less as a ligand.

Efficiency phosphorescent OLEDs with a low roll-off based on a hetero-triplet iridium complex

In order to explore the triplet-triplet annihilation in cyclometalated iridium complexes, a hetero-triplet iridium complex [Ir(ppy)2pbi] employing two 2-phenylpyridine (Hppy) ligands and one 1,2-diphenyl-1H-benzo[d]-imidazole (Hpbi) ligand with

Facile synthesis and complete characterization of homoleptic and heteroleptic cyclometalated Iridium(III) complexes for photocatalysis

Herein we describe an improved synthesis for homoleptic iridium(III) 2-phenylpyridine based photocatalysts that allows rapid access to these compounds in good to high yields which have recently become a vital component within the field of catalysis. In addition, we synthesized a number of heteroleptic iridium(III) 2-phenylpyridine photocatalysts and report their photophysical and electrochemical properties. The emission energies span the range of 473-560 nm and reduction potentials from -2.27 V to -1.23 V and oxidation potentials ranging from 1.81 V to 0.69 V. Additionally, we provide the calculated excited state properties and comment on the role of these properties in designing catalytic cycles.

Preparation of luminescent iridium complexes and precursors thereof

In the present invention, novel synthetic processes for preparing luminescent iridium complexes and precursors thereof are provided. The method employs water as the reaction solvent to prepare luminescent iridium complexes in two different ways. In the first way, a precursor [Ir2(C11NR8)4I2] (Formula I) is prepared from one of IrCl3, M3IrCl6 (M=Li, Na, K) and [Ir2(C11NR8)4Cl2], and then the precursor [Ir2(C11NR8)4I2] is converted into luminescent iridium complexes [Ir(C11NR8)2(C11NR′8)] (Formula II). In the second way, a metal complex IrCl3 or M3IrCl6 (M=Li, Na, K), HC11NR8 and a base are converted directly into the iridium complexes [Ir(C11NR8)3] (Formula VIII). Herein, R and R′ are defined the same as the specification.