2-Phenylpyridine

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).^[1]

2-Phenylpyridine

Names
Preferred IUPAC name 2-Phenylpyridine
Other names 2-Azabiphenyl
Identifiers
CAS Number	1008-89-5
3D model (JSmol)	Interactive image
ChemSpider	13286
ECHA InfoCard	100.012.512
EC Number	213-763-1
MeSH	C058324
PubChem CID	13887
UNII	2Y6S09838Q Y
CompTox Dashboard (EPA)	DTXSID6074417
InChI InChI=1S/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9H Key: VQGHOUODWALEFC-UHFFFAOYSA-N InChI=1/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9H Key: VQGHOUODWALEFC-UHFFFAOYAS
SMILES c1ccc(cc1)c2ccccn2
Properties
Chemical formula	C11H9N
Molar mass	155.200 g·mol−1
Appearance	Colorless oil
Density	1.086 g/mL
Boiling point	268–270 °C (514–518 °F; 541–543 K)
Solubility in water	Low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The compound is prepared by the reaction of phenyl lithium with pyridine:^[2]

C₆H₅Li + C₅H₅N → C₆H₅-C₅H₄N + LiH

The reaction of iridium trichloride with 2-phenylpyridine proceeds via cyclometallation to give the chloride-bridged complex:^[3][4]

4 C₆H₅-C₅H₄N + 2 IrCl₃(H₂O)₃ → Ir₂Cl₂(C₆H₄-C₅H₄N)₄ + 4 HCl

This complex can be converted to the pictured tris(cyclometallated) derivative tris(2-phenylpyridine)iridium.

Structure of Ir(C₆H₄-C₅H₄N)₃

The degree and regiochemistry of fluorination of metalated 2-phenylpyridine ligands in platinum(II) complexes significantly modifies the emission properties of the complexes.^[5]

References

1. Eli Zysman-Colman, ed. (2017). Iridium(III) in Optoelectronic and Photonics Applications. John Wiley & Sons. ISBN 978-1-119-00713-5.
2. Evans, J. C. W.; Allen, C. F. H. (1938). "2-Phenylpyridine". Organic Syntheses. 18: 70. doi:10.15227/orgsyn.018.0070.
3. Lamansky, S.; Djurovich, P.; Murphy, D.; et al. (2001). "Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes". Inorganic Chemistry. 40 (7): 1704–1711. doi:10.1021/ic0008969. PMID 11261983.
4. Kip A. Teegardin, Jimmie D. Weaver (2018). "Preparation of Fac-Tris(2-Phenylpyridinato) Iridium(III)". Org. Synth. 95: 29–45. doi:10.15227/orgsyn.095.0029. PMC 6022758. PMID 29962554.
5. Thompson ME, Djurovich PE, Barlow S, Marder S (2007). "Organometallic Complexes for Optoelectronic Applications". Comprehensive Organometallic Chemistry III. Vol. 12. pp. 101–194. doi:10.1016/B0-08-045047-4/00169-2. ISBN 978-0-08-045047-6.

Further reading

• Zhou, Guijiang; Wong, Wai-Yeung; Yang, Xiaolong (2011). "New Design Tactics in OLEDs Using Functionalized 2-Phenylpyridine-Type Cyclometalates of Iridium(III) and Platinum(II)". Chemistry: An Asian Journal. 6 (7): 1706–1727. doi:10.1002/asia.201000928. PMID 21557486.