Triphenylene

Triphenylene
Names
	Preferred IUPAC name Triphenylene
	Other names Benzo[l]phenanthrene; 9,10-Benzophenanthrene; 1,2,3,4-Dibenzonaphthalene; Isochrysene
Identifiers
CAS Number	217-59-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33080 ;
ChEMBL	ChEMBL1797416 ;
ChemSpider	8816 ;
ECHA InfoCard	100.005.385
EC Number	205-922-9;
KEGG	C19541 ;
MeSH	C009590
PubChem CID	9170;
UNII	18WX3373I0 ;
CompTox Dashboard (EPA)	DTXSID9059757 ;
	InChI 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 Key: SLGBZMMZGDRARJ-UHFFFAOYSA-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;
	SMILES c1(cccc3)c3c(cccc4)c4c2c1cccc2;
Properties
Chemical formula	C18H12
Molar mass	228.294 g·mol−1
Appearance	white
Density	1.308 g/cm3
Melting point	198 °C; 388 °F; 471 K
Boiling point	438 °C; 820 °F; 711 K
Magnetic susceptibility (χ)	-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). verify (what is ?) Infobox references

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 D_3h. It is a white or colorless solid.

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

^ 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.
^ Ahmed, F. R.; Trotter, J. (1963). "The crystal structure of triphenylene". Acta Crystallographica. 16 (6): 503–508. Bibcode:1963AcCry..16..503A. doi:10.1107/S0365110X63001365.
^ Heaney, H.; Millar, I. T. (1960). "Triphenylene". Organic Syntheses. 40: 105. doi:10.15227/orgsyn.040.0105.
^ 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)
^ 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.
^ 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

External links

Polycyclic Aromatic Hydrocarbon Structure Index Archived 2008-02-15 at the Wayback Machine

[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. Bibcode:1963AcCry..16..503A. 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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v t e Polycyclic aromatic hydrocarbons
2 rings	Butalene Azulene Naphthalene
3 rings	Acenaphthene Acenaphthylene Anthracene Fluorene Phenalene Phenanthrene
4 rings	Benz[a]anthracene Benzo[a]fluorene Benzo[c]fluorene Benzo[c]phenanthrene Chrysene Fluoranthene Pyrene Tetracene Triphenylene Tricyclobutabenzene
5 rings	Benz[e]acephenanthrylene Benzopyrene Benzo[a]pyrene Benzo[e]pyrene 6H-Benzo[cd]pyrene(Olympicene) Benzo[a]fluoranthene Benzo[b]fluoranthene Benzo[j]fluoranthene Benzo[k]fluoranthene trans-Bicalicene Dibenz[a,h]anthracene Dibenz[a,j]anthracene Pentacene Perylene Picene Tetraphenylene
6 rings	Anthanthrene Benzo[ghi]perylene Corannulene Dibenzopyrenes Hexacene Triangulene Zethrene
7+ rings	Coronene Dicoronylene Diindenoperylene Heptacene Hexabenzocoronene (Hexa-cata-) Kekulene Ovalene Rubicene Rubrene Sumanene Superphenalene Trinaphthylene Truxene
General classes	Acene Circulene Cyclacene Helicene Phenacene