Iridium acetylacetonate

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Iridium acetylacetonate
Ir(acac)3.png
Identifiers
3D model (JSmol)
ECHA InfoCard 100.036.086 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • CC(=O)C=C(C)[O-].CC(=O)C=C(C)[O-].CC(=O)C=C(C)[O-].[Ir+3]
Properties
C15H21IrO6
Molar mass 489.544 g·mol−1
Appearanceorange solid [1]
Melting point 269 to 271 °C (516 to 520 °F; 542 to 544 K) (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Iridium acetylacetonate is the iridium coordination complex with the formula Ir(O2C5H7)3, which is sometimes known as Ir(acac)3. The molecule has D3-symmetry. [2] It is a yellow-orange solid that is soluble in organic solvents.

Contents

Preparation and isomerism

It is prepared from IrCl3(H2O)3 and acetylacetone. [3] The complex has been resolved into individual enantiomers by separation of its adduct with dibenzoyltartaric acid. [4]

A second linkage isomers is also known. In the second isomer one of the acetylacetonate ligands is bonded to Ir through carbon. [5]

Structures of C-bonded "Ir(acac)3" C-bondedIr-acac.png
Structures of C-bonded "Ir(acac)3"

Uses

The O6-bonded isomer has been investigated for use chemical vapor deposition (CVD). One example is the deposition of red phosphorescent emitter compounds used in OLEDs. [6] [7]

The C-bonded isomer has been investigated as a catalyst for C-H activation reactions. [5]

Related Research Articles

Phosphorescent organic light-emitting diodes (PHOLED) are a type of organic light-emitting diode (OLED) that use the principle of phosphorescence to obtain higher internal efficiencies than fluorescent OLEDs. This technology is currently under development by many industrial and academic research groups.

<span class="mw-page-title-main">Tungsten dichloride dioxide</span> Chemical compound

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<span class="mw-page-title-main">Chromium(III) acetylacetonate</span> Chemical compound

Chromium(III) acetylacetonate is the coordination compound with the formula Cr(C5H7O2)3, sometimes designated as Cr(acac)3. This purplish coordination complex is used in NMR spectroscopy as a relaxation agent because of its solubility in nonpolar organic solvents and its paramagnetism.

<span class="mw-page-title-main">Organoiridium chemistry</span> Chemistry of organometallic compounds containing an iridium-carbon bond

Organoiridium chemistry is the chemistry of organometallic compounds containing an iridium-carbon chemical bond. Organoiridium compounds are relevant to many important processes including olefin hydrogenation and the industrial synthesis of acetic acid. They are also of great academic interest because of the diversity of the reactions and their relevance to the synthesis of fine chemicals.

<span class="mw-page-title-main">Nickel(II) bis(acetylacetonate)</span> Coordination complex

Nickel(II) bis(acetylacetonate) is a coordination complex with the formula [Ni(acac)2]3, where acac is the anion C5H7O2 derived from deprotonation of acetylacetone. It is a dark green paramagnetic solid that is soluble in organic solvents such as toluene. It reacts with water to give the blue-green diaquo complex Ni(acac)2(H2O)2.

<span class="mw-page-title-main">Ruthenium(III) acetylacetonate</span> Chemical compound

Ruthenium(III) acetylacetonate is a coordination complex with the formula Ru(O2C5H7)3. O2C5H7 is the ligand called acetylacetonate. This compound exists as a dark violet solid that is soluble in most organic solvents. It is used as a precursor to other compounds of ruthenium.

Metal acetylacetonates are coordination complexes derived from the acetylacetonate anion (CH
3
COCHCOCH
3
) and metal ions, usually transition metals. The bidentate ligand acetylacetonate is often abbreviated acac. Typically both oxygen atoms bind to the metal to form a six-membered chelate ring. The simplest complexes have the formula M(acac)3 and M(acac)2. Mixed-ligand complexes, e.g. VO(acac)2, are also numerous. Variations of acetylacetonate have also been developed with myriad substituents in place of methyl (RCOCHCOR). Many such complexes are soluble in organic solvents, in contrast to the related metal halides. Because of these properties, acac complexes are sometimes used as catalyst precursors and reagents. Applications include their use as NMR "shift reagents" and as catalysts for organic synthesis, and precursors to industrial hydroformylation catalysts. C
5
H
7
O
2
in some cases also binds to metals through the central carbon atom; this bonding mode is more common for the third-row transition metals such as platinum(II) and iridium(III).

<span class="mw-page-title-main">Metal bis(trimethylsilyl)amides</span>

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<span class="mw-page-title-main">Tris(dimethylamino)aluminium dimer</span> Chemical compound

Tris(dimethylamino)aluminium dimer, formally bis(μ-dimethylamino)tetrakis(dimethylamino)dialuminium, is an amide complex of aluminium. This compound may be used as a precursor to other aluminium complexes.

Barium acetylacetonate is a compound with formula Ba(C5H7O2)2. It is the Ba2+ complex of the anion acetylacetonate. The compound is typically encountered as an ill-defined hydrate, which would accord with the high coordination number characteristic of barium.

Metal-catalyzed C–H borylation reactions are transition metal catalyzed organic reactions that produce an organoboron compound through functionalization of aliphatic and aromatic C–H bonds and are therefore useful reactions for carbon–hydrogen bond activation. Metal-catalyzed C–H borylation reactions utilize transition metals to directly convert a C–H bond into a C–B bond. This route can be advantageous compared to traditional borylation reactions by making use of cheap and abundant hydrocarbon starting material, limiting prefunctionalized organic compounds, reducing toxic byproducts, and streamlining the synthesis of biologically important molecules. Boronic acids, and boronic esters are common boryl groups incorporated into organic molecules through borylation reactions. Boronic acids are trivalent boron-containing organic compounds that possess one alkyl substituent and two hydroxyl groups. Similarly, boronic esters possess one alkyl substituent and two ester groups. Boronic acids and esters are classified depending on the type of carbon group (R) directly bonded to boron, for example alkyl-, alkenyl-, alkynyl-, and aryl-boronic esters. The most common type of starting materials that incorporate boronic esters into organic compounds for transition metal catalyzed borylation reactions have the general formula (RO)2B-B(OR)2. For example, bis(pinacolato)diboron (B2Pin2), and bis(catecholato)diborane (B2Cat2) are common boron sources of this general formula.

<span class="mw-page-title-main">Potassium octachlorodirhenate</span> Chemical compound

Potassium octachlorodirhenate(III) is an inorganic compound with the formula K2Re2Cl8. This dark blue salt is well known as an early example of a compound featuring quadruple bond between its metal centers. Although the compound has no practical value, its characterization was significant in opening a new field of research into complexes with quadruple bonds.

<span class="mw-page-title-main">2-Phenylpyridine</span> Chemical compound

2-Phenylpyridine is an organic compound with the formula C6H5C5H4N (or C11H9N). It is a colourless viscous liquid. The compound and related derivatives have attracted interest as precursors to highly fluorescent metal complexes of possible value as organic light emitting diodes (OLEDs).

The fluorosulfates or fluorosulfonates are a set of salts of fluorosulfuric acid with an ion formula SO3F. The fluorosulfate anion can be treated as though it were a hydrogen sulfate anion with hydroxyl substituted by fluorine. The fluorosulfate ion has a low propensity to form complexes with metal cations. Since fluorine is similar in size to oxygen, the fluorosulfate ion is roughly tetrahedral and forms salts similar to those of the perchlorate ion. It is isoelectronic with sulfate, SO-20−
4
. When an organic group is substituted for the anions, organic fluorosulfonates are formed.

Mark E. Thompson is a Californian chemistry academic who has worked with OLEDs.

<span class="mw-page-title-main">Rhodium acetylacetonate</span> Chemical compound

Rhodium acetylacetonate is the coordination complex with the formula Rh(C5H7O2)3, which is sometimes known as Rh(acac)3. The molecule has D3-symmetry. It is a yellow-orange solid that is soluble in organic solvents.

<span class="mw-page-title-main">Sodium 1,3-dithiole-2-thione-4,5-dithiolate</span> Chemical compound

Sodium 1,3-dithiole-2-thione-4,5-dithiolate is the organosulfur compound with the formula Na2C3S5, abbreviated Na2dmit. It is the sodium salt of the conjugate base of the 1,3-dithiole-2-thione-4,5-dithiol. The salt is a precursor to dithiolene complexes and tetrathiafulvalenes.

<span class="mw-page-title-main">Transition metal chloride complex</span> Coordination complex

In chemistry, a transition metal chloride complex is a coordination complex that consists of a transition metal coordinated to one or more chloride ligand. The class of complexes is extensive.

<span class="mw-page-title-main">Tris(2-phenylpyridine)iridium</span> Chemical compound

Tris(2-phenylpyridine)iridium, abbreviated [Ir(ppy)3] is the organoiridium complex with the formula Ir(C6H4-C5H4N)3. The complex, a yellow-green solid, is a derivative of Ir3+ bound to three monoanionic 2-pyridinylphenyl ligands. It is electroluminescent, emitting green light. The complex is observed with the facial stereochemistry, which is chiral.

<span class="mw-page-title-main">Transition metal ether complex</span>

In chemistry, a transition metal ether complex is a coordination complex consisting of a transition metal bonded to one or more ether ligand. The inventory of complexes is extensive. Common ether ligands are diethyl ether and tetrahydrofuran. Common chelating ether ligands include the glymes, dimethoxyethane (dme) and diglyme, and the crown ethers. Being lipophilic, metal-ether complexes often exhibit solubility in organic solvents, a property of interest in synthetic chemistry. In contrast, the di-ether 1,4-dioxane is generally a bridging ligand.

References

  1. Iridium acetylacetonate
  2. V. G. Isakova, I. A. Baidina, N. B. Morozova, I. K. Igumenov "γ-Halogenated iridium(III) Acetylacetonates" Polyhedron 2000, Volume 19, Pages 1097–1103. doi : 10.1016/S0277-5387(00)00358-2
  3. James E. Collins, Michael P. Castellani, Arnold L. Rheingold, Edward J. Miller, William E. Geiger, Anne L. Rieger, Philip H. Rieger "Synthesis, Characterization, and Molecular Structure of Bis(tetraphenylcyclopentdienyl)rhodium(II)" Organometallics 1995, pp 1232–1238. doi : 10.1021/om00003a025
  4. Drake, A. F.; Gould, J. M.; Mason, S. F.; Rosini, C.; Woodley, F. J. (1983). "The optical resolution of tris(pentane-2,4-dionato)metal(III) complexes". Polyhedron. 2 (6): 537–538. doi:10.1016/S0277-5387(00)87108-9.
  5. 1 2 S. M. Bischoff; R. A. Periana (2010). Oxygen and Carbon Bound Acetylacetonato Iridium(III) Complexes. Inorganic Syntheses. Vol. 35. p. 173. doi:10.1002/9780470651568. ISBN   978-0-470-65156-8.
  6. "Synthesis of a high-efficiency red phosphorescent emitter for organic light-emitting diodes"
  7. "Highly Phosphorescent Bis-Cyclometalated Iridium Complexes:  Synthesis, Photophysical Characterization, and Use in Organic Light Emitting Diodes"