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2-Phenylpyridine

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2-Phenylpyridine
Names
Preferred IUPAC name 2-Phenylpyridine
Other names 2-Azabiphenyl
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.512 Edit this at Wikidata
EC Number
  • 213-763-1
MeSH C058324
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9HKey: VQGHOUODWALEFC-UHFFFAOYSA-N
  • InChI=1/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9HKey: VQGHOUODWALEFC-UHFFFAOYAS
SMILES
  • c1ccc(cc1)c2ccccn2
Properties
Chemical formula C11H9N
Molar mass 155.200 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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).

The compound is prepared by the reaction of phenyl lithium with pyridine:

C6H5Li + C5H5N → C6H5-C5H4N + LiH

The reaction of iridium trichloride with 2-phenylpyridine proceeds via cyclometallation to give the chloride-bridged complex:

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.

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.
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