Tris(2-phenylpyridine)iridium

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.

Tris(2-phenylpyridine)iridium
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 Edit this at Wikidata
  • 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
Appearance yellow-green solid
Hazards
GHS labelling:
GHS07: Exclamation mark
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).

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]

References

edit
  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.