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2-Phenylpyridine

2-Phenylpyridine is an organic compound with the formula C<sub>6</sub>H<sub>5</sub>C<sub>5</sub>H<sub>4</sub>N (or C<sub>11</sub>H<sub>9</sub>N). 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:

C<sub>6</sub>H<sub>5</sub>Li + C<sub>5</sub>H<sub>5</sub>N → C<sub>6</sub>H<sub>5</sub>-C<sub>5</sub>H<sub>4</sub>N + LiH

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

4 C<sub>6</sub>H<sub>5</sub>-C<sub>5</sub>H<sub>4</sub>N + 2 IrCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> → Ir<sub>2</sub>Cl<sub>2</sub>(C<sub>6</sub>H<sub>4</sub>-C<sub>5</sub>H<sub>4</sub>N)<sub>4</sub> + 4 HCl

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

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

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Further reading