Tris(2-phenylpyridine)iridium

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
CAS Number	94928-86-6 [ChemSpider];
ChemSpider	19285809;
ECHA InfoCard	100.163.509
PubChem CID	45358635 (formula wrong);
CompTox Dashboard (EPA)	DTXSID10464270 ;
	InChI InChI=1S/3C11H8N.Ir/c31-2-6-10(7-3-1)11-8-4-5-9-12-11;/h31-6,8-9H; Key: QKBWDYLFYVXTGE-UHFFFAOYSA-N;
Properties
Chemical formula	C33H24IrN3
Molar mass	654.793 g·mol−1
Appearance	yellow-green solid
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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]

References

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.
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.
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.

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[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.