Triphenylene

Triphenylene is an organic compound with the formula (C6H4)3. A flat polycyclic aromatic hydrocarbon (PAH), it consists of four fused benzene rings. Triphenylene has delocalized 18-π-electron systems based on a planar structure, corresponding to the symmetry group D3h. It is a white or colorless solid.

Triphenylene
Skeletal formula with numbering convention
Ball-and-stick model
Names
Preferred IUPAC name
Triphenylene[1]
Other names
Benzo[l]phenanthrene
9,10-Benzophenanthrene
1,2,3,4-Dibenzonaphthalene
Isochrysene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.385
EC Number
  • 205-922-9
KEGG
MeSH C009590
UNII
  • InChI=1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H ☒N
    Key: SLGBZMMZGDRARJ-UHFFFAOYSA-N ☒N
  • InChI=1/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
  • c1(cccc3)c3c(cccc4)c4c2c1cccc2
Properties
C18H12
Molar mass 228.294 g·mol−1
Appearance white
Density 1.308 g/cm3[2]
Melting point 198 °C; 388 °F; 471 K
Boiling point 438 °C; 820 °F; 711 K
-156.6·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Preparation

Triphenylene can be isolated from coal tar. It can also be synthesized in various ways. One method is trimerization of benzyne.[3] Another method involves trapping benzyne with a biphenyl derivative.[4]

Properties

Triphenylene is more resonance stable than its isomers chrysene, benz[a]anthracene, benzo[c]phenanthrene, and tetracene. For this reason triphenylene resists hydrogenation.[5]

As a disc-shaped, planar molecule, triphenylene has attracted attention as the core of discotic mesogen in liquid crystalline materials.[6]

References
  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 209. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. Ahmed, F. R.; Trotter, J. (1963). "The crystal structure of triphenylene". Acta Crystallographica. 16 (6): 503–508. doi:10.1107/S0365110X63001365.
  3. Heaney, H.; Millar, I. T. (1960). "Triphenylene". Organic Syntheses. 40: 105. doi:10.15227/orgsyn.040.0105.
  4. Katie A. Spence, Milauni M. Mehta, Neil K. Garg (2022). "Synthesis of Triphenylene via the Palladium–Catalyzed Annulation of Benzyne". Organic Syntheses. 99: 174–189. doi:10.15227/orgsyn.099.0174. S2CID 250383238.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Kofman, V.; Sarre, P.J.; Hibbins, R.E.; ten Kate, I.L.; Linnartz, H. (2017). "Laboratory spectroscopy and astronomical significance of the fully-benzenoid PAH triphenylene and its cation". Molecular Astrophysics. 7: 19–26. Bibcode:2017MolAs...7...19K. doi:10.1016/j.molap.2017.04.002. hdl:1887/58655. S2CID 67834616.
  6. Janietz, Dietmar (2001), "Liquid Crystals at Interfaces", Handbook of Surfaces and Interfaces of Materials, Elsevier, pp. 436–437, doi:10.1016/b978-012513910-6/50014-1, ISBN 978-0-12-513910-6, retrieved 2020-08-23
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