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
IUPAC name
2-Phenylpyridine
Other names
2-Azabiphenyl
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.512
EC Number
  • 213-763-1
MeSH C058324
UNII
Properties
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)
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.

Structure of Ir(C6H4-C5H4N)3

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. doi:10.15227/orgsyn.095.0029.

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.
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