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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
Preferred IUPAC name
2-Phenylpyridine
Other names
2-Azabiphenyl
Identifiers
  • 1008-89-5
3D model (JSmol)
  • Interactive image
ChemSpider
  • 13286
ECHA InfoCard 100.012.512
EC Number
  • 213-763-1
MeSH C058324
  • 13887
UNII
  • 2Y6S09838Q Y
  • DTXSID6074417
  • InChI=1S/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9H
    Key: VQGHOUODWALEFC-UHFFFAOYSA-N
  • InChI=1/C11H9N/c1-2-6-10(7-3-1)11-8-4-5-9-12-11/h1-9H
    Key: VQGHOUODWALEFC-UHFFFAOYAS
  • c1ccc(cc1)c2ccccn2
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).

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 tris(2-phenylpyridine)iridium.

Structure of Ir(C6H4-C5H4N)3

References edit

  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.

Further reading edit

  • 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.

phenylpyridine, organic, compound, with, formula, c6h5c5h4n, c11h9n, colourless, viscous, liquid, compound, related, derivatives, have, attracted, interest, precursors, highly, fluorescent, metal, complexes, possible, value, organic, light, emitting, diodes, o. 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 Preferred IUPAC name 2 Phenylpyridine Other names 2 Azabiphenyl Identifiers CAS Number 1008 89 5 3D model JSmol Interactive image ChemSpider 13286 ECHA InfoCard 100 012 512 EC Number 213 763 1 MeSH C058324 PubChem CID 13887 UNII 2Y6S09838Q Y CompTox Dashboard EPA DTXSID6074417 InChI InChI 1S C11H9N c1 2 6 10 7 3 1 11 8 4 5 9 12 11 h1 9HKey VQGHOUODWALEFC UHFFFAOYSA NInChI 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 C 11H 9N 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 Solubility in water 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 tris 2 phenylpyridine iridium Structure of Ir C6H4 C5H4N 3References edit Eli Zysman Colman ed 2017 Iridium III in Optoelectronic and Photonics Applications John Wiley amp Sons ISBN 978 1 119 00713 5 Evans J C W Allen C F H 1938 2 Phenylpyridine Organic Syntheses 18 70 doi 10 15227 orgsyn 018 0070 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 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 Further reading editZhou 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 Retrieved from https en wikipedia org w index php title 2 Phenylpyridine amp oldid 1195319319, wikipedia, wiki, book, books, library,

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