Tris(2-phenylpyridine)iridium

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Tris(2-phenylpyridine)iridium
Ir(ppy) Schematic.png
Names
Other names
tris(2-phenylpyridine)iridium, Tris[2-(2-pyridinyl)phenyl]iridium, Tris[2-(2-pyridinyl)phenyl-C,N]iridium
Identifiers
ChemSpider
ECHA InfoCard 100.163.509 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/3C11H8N.Ir/c3*1-2-6-10(7-3-1)11-8-4-5-9-12-11;/h3*1-6,8-9H;
    Key: QKBWDYLFYVXTGE-UHFFFAOYSA-N
Properties
C33H24IrN3
Molar mass 654.793 g·mol−1
Appearanceyellow-green solid
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

The complex is prepared by cyclometalation reactions of 2-phenylpyridine and iridium trichloride, as represented by this idealized equation: [1] [2]

IrCl3 + 3 C6H5-C5H4N → Ir(C6H4-C5H4N)3 + 3 HCl

The complex and many analogues have been investigated for application in photoredox catalysis. Its excited state has a reduction potential of −2.14 V, nearly 1 V more negative than the reduction potential of excited [Ru(bipy)3]2+. [3]

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3
COCHCOCH
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) 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
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H
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References

  1. Lamansky, Sergey; Djurovich, Peter; Murphy, Drew; Abdel-Razzaq, Feras; Kwong, Raymond; Tsyba, Irina; Bortz, Manfred; Mui, Becky; Bau, Robert; Thompson, Mark E. (2001). "Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes". Inorganic Chemistry. 40 (7): 1704–1711. doi:10.1021/ic0008969. PMID   11261983.
  2. Dedeian, K.; Djurovich, P. I.; Garces, F. O.; Carlson, G.; Watts, R. J. (1991). "A new synthetic route to the preparation of a series of strong photoreducing agents: Fac-tris-ortho-metalated complexes of iridium(III) with substituted 2-phenylpyridines". Inorganic Chemistry. 30 (8): 1685–1687. doi:10.1021/ic00008a003.
  3. Koike, Takashi; Akita, Munetaka (2016). "Fine Design of Photoredox Systems for Catalytic Fluoromethylation of Carbon–Carbon Multiple Bonds". Accounts of Chemical Research. 49 (9): 1937–1945. doi: 10.1021/acs.accounts.6b00268 . PMID   27564676.