2-Phenylpyridine

2-phenylpyridine.png 80 skin-invert 2-phenylpyridine-based-on-xtal-and-DFT-3D-sf.png 100 bg-transparent 2-Phenylpyridine 2-Azabiphenyl 1008-89-5 correct FDA 2Y6S09838Q 213-763-1 13887 13286 c1ccc(cc1)c2ccccn2 1/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9H VQGHOUODWALEFC-UHFFFAOYAS 1S/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9H VQGHOUODWALEFC-UHFFFAOYSA-N C058324 11 9 1 Colorless oil 1.086 g/mL 268–270 Low 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).Iridium(III) in Optoelectronic and Photonics Applications Eli Zysman-Colman 2017 John Wiley & Sons 978-1-119-00713-5 The compound is prepared by the reaction of phenyl lithium with pyridine:Evans J. C. W. Allen C. F. H. 2-Phenylpyridine Organic Syntheses 1938 18 70 10.15227/orgsyn.018.0070 free C6H5Li + C5H5N → C6H5-C5H4N + LiH The reaction of iridium trichloride with 2-phenylpyridine proceeds via cyclometallation to give the chloride-bridged complex:Lamansky, S. Djurovich, P. Murphy, D. Abdel-Razzaq, F. Kwong, R. Tsyba, I. Bortz, M. Mui, B. Bau, R. Thompson, M. E. 3 Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes Inorganic Chemistry 2001 40 7 1704–1711 10.1021/ic0008969 11261983Preparation of Fac-Tris(2-Phenylpyridinato) Iridium(III) Kip A. Teegardin, Jimmie D. Weaver Org. Synth. 2018 95 29–45 10.15227/orgsyn.095.0029 free 29962554 6022758 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. thumb|left|Structure of Ir(C6H4-C5H4N)3left The degree and regiochemistry of fluorination of metalated 2-phenylpyridine ligands in platinum(II) complexes significantly modifies the emission properties of the complexes. Thompson ME, Djurovich PE, Barlow S, Marder S Organometallic Complexes for Optoelectronic Applications Comprehensive Organometallic Chemistry III 2007 12 101–194 10.1016/B0-08-045047-4/00169-2 978-0-08-045047-6 References Further reading Zhou Guijiang Wong Wai-Yeung Yang Xiaolong New Design Tactics in OLEDs Using Functionalized 2-Phenylpyridine-Type Cyclometalates of Iridium(III) and Platinum(II) Chemistry: An Asian Journal 2011 6 7 1706–1727 10.1002/asia.201000928 21557486 Category:2-Pyridyl compounds Category:Photochemistry Category:Ligands Category:Phenyl compounds