2-Phenylpyridine is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

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 complex A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many ...

es of possible value as

organic light emitting diode An organic light-emitting diode (OLED or organic LED), also known as organic electroluminescent (organic EL) diode, is a light-emitting diode (LED) in which the emissive electroluminescent layer is a film of organic compound that emits light i ...

s (OLEDs). The compound is prepared by the reaction of

phenyl lithium Phenyllithium or lithobenzene is an organometallic agent with the empirical formula C6H5Li. It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic synth ...

with pyridine: :C₆H₅Li + C₅H₅N → C₆H₅-C₅H₄N + LiH The reaction of

iridium trichloride Iridium(III) chloride is the inorganic compound with the formula IrCl3. The anhydrous compound is relatively rare, but the related hydrate is useful for preparing other iridium compounds. The anhydrous salt is a dark green crystalline solid. ...

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. Ir(ppy) Schematic

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Further reading