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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 450122676
| Watchedfields = changed
| ImageFile = Triphenylene_chemical_structure.png
⚫ | verifiedrevid = 455515671
⚫ | ImageSize = 180px
⚫ | ImageFile = Triphenylene V2.svg
⚫ | ImageName = Skeletal formula with numbering convention
⚫ | ImageSize = 150px
⚫ | ImageFile1 = Triphenylene-3D-balls.png
⚫ | ImageName = Skeletal formula with numbering convention
⚫ | ImageSize1 = 180px
| ImageFile1 = Triphenylene-3D-balls.png
⚫ | ImageName1 = Ball-and-stick model
| ImageFile2 = Triphenylene_crystals.jpg
| IUPACName = triphenylene
⚫ | ImageSize1 = 180px
⚫ | OtherNames = benzophenanthrene, 9,10-benzophenanthrene, 1,2,3,4-dibenznaphthalene, isochrysene
⚫ | ImageName1 = Ball-and-stick model
⚫ | Section1 = {{Chembox Identifiers
| PIN = Triphenylene<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=209 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
⚫ | CASNo_Ref = {{cascite}}
⚫ | OtherNames = Benzophenanthrene<br />9,10-Benzophenanthrene<br />1,2,3,4-Dibenzonaphthalene<br />Isochrysene
| CASNo = 217-59-4
⚫ | Section1 = {{Chembox Identifiers
⚫ | PubChem = 9170
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | 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
| PubChem = | CASNo = 217-59-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 18WX3373I0
⚫ | PubChem = 9170
⚫ | 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
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 33080
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1797416
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19541 | KEGG = C19541
| SMILES = C1(C=CC=C3)=C3C(C=CC=C4)=C4C2=C1C=CC=C2 | SMILES = c1(cccc3)c3c(cccc4)c4c2c1cccc2
| MeSHName = C009590
⚫ }}
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | Section2 = {{Chembox Properties
| StdInChI = 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
⚫ | C=18|H=12
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ | Appearance =
| StdInChIKey = SLGBZMMZGDRARJ-UHFFFAOYSA-N
| Density =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8816
| EINECS = 205-922-9
⚫ }}
⚫ | Section2 = {{Chembox Properties
⚫ | C=18 | H=12
⚫ | Appearance = white
| Density = 1.308 g/cm<sup>3</sup><ref>{{cite journal |doi=10.1107/S0365110X63001365|title=The crystal structure of triphenylene |year=1963 |last1=Ahmed |first1=F. R. |last2=Trotter |first2=J. |journal=Acta Crystallographica |volume=16 |issue=6 |pages=503–508 |doi-access=free |bibcode=1963AcCry..16..503A }}</ref>
| MeltingPtK = 471 | MeltingPtK = 471
| BoilingPtK = 711 | BoilingPtK = 711
| Solubility = }} | Solubility =
| MagSus = -156.6·10<sup>−6</sup> cm<sup>3</sup>/mol }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt =
}}
}} }}


In ], the ] '''triphenylene''' is a flat ] (PAH) consisting of four fused ] rings. Triphenylene can be isolated from ], but it is also made synthetically using benzyn chemistry. One molecule of triphenylene has delocalized 18-''π''-electron systems based on a planar structure. It has the molecular formula {{chem|C|18|H|12}}. '''Triphenylene''' is an ] with the formula (C<sub>6</sub>H<sub>4</sub>)<sub>3</sub>. A flat ] (PAH), it consists of four fused ] rings. Triphenylene has delocalized 18-''π''-electron systems based on a planar structure, corresponding to the ] ''D''<sub>3h</sub>. It is a white or colorless solid.


==Preparation==
Triphenylene is a fully benzenoid PAH, meaning its structure is composed only of full benzene rings interconnected by ] single bonds. The three benzene rings can be drawn as the three outer rings, with the central ring formed by one face of each and the three carbon-carbon single bonds.
Triphenylene can be isolated from ]. It can also be synthesized in various ways. One method is ] of ].<ref>{{OrgSynth |first1=H. |last1=Heaney |first2=I. T. |last2=Millar |year=1960 |title=Triphenylene |volume=40 |pages=105 |doi=10.15227/orgsyn.040.0105}}</ref> Another method involves trapping benzyne with a biphenyl derivative.<ref>{{cite journal |doi=10.15227/orgsyn.099.0174|author=Katie A. Spence, Milauni M. Mehta, Neil K. Garg| title=Synthesis of Triphenylene via the Palladium–Catalyzed Annulation of Benzyne |year=2022 |journal=Organic Syntheses |volume=99 |pages=174–189|s2cid=250383238 |doi-access=free }}</ref>


== Properties ==
Being a fully bezenoid PAH means that triphenylene is much more ] stable than its isomers ], anthracene]], phenanthrene]], and ]. This makes it much more difficult to hydrogenate to the ].
Triphenylene is more ] stable than its isomers ], anthracene]], phenanthrene]], and ]. For this reason triphenylene resists ].<ref>{{Cite journal|last1=Kofman|first1=V.|last2=Sarre|first2=P.J.|last3=Hibbins|first3=R.E.|last4=ten Kate|first4=I.L.|last5=Linnartz|first5=H.|date=2017|title=Laboratory spectroscopy and astronomical significance of the fully-benzenoid PAH triphenylene and its cation|url=https://linkinghub.elsevier.com/retrieve/pii/S2405675817300039|journal=Molecular Astrophysics|language=en|volume=7|pages=19–26|doi=10.1016/j.molap.2017.04.002|bibcode=2017MolAs...7...19K |hdl=1887/58655|s2cid=67834616 |hdl-access=free}}</ref>


As a disc-shaped, planar molecule, triphenylene has attracted attention as the core of discotic ] in ]line materials.<ref>{{Citation|last=Janietz|first=Dietmar|title=Liquid Crystals at Interfaces|date=2001|url=https://linkinghub.elsevier.com/retrieve/pii/B9780125139106500141|work=Handbook of Surfaces and Interfaces of Materials|pages=436–437|publisher=Elsevier|language=en|doi=10.1016/b978-012513910-6/50014-1|isbn=978-0-12-513910-6|access-date=2020-08-23}}</ref>
In light of these characteristics, triphenylene may have uses in ] and ]. Triphenylene is a disc-shaped molecule with a planar structure and three-fold rotation axes. Consisting of colorless needle-like crystals, it emits bluish purple ] by ] irradiation.{{Fact|date=September 2011}}
⚫ == References ==
{{reflist}}


== External links ==
In terms of its ], the symmetry of triphenylene is classified as ''D<sub>3h</sub>'' in ]. Because of these characteristics, six-fold (in the 2, 3, 6, 7, 10, and 11 positions) alkyloxy- or alkylthiol-substituted triphenylenes can be used as a discotic ] in ]line materials.
⚫ * {{Webarchive|url=https://web.archive.org/web/20080215085302/http://ois.nist.gov/pah/sp922_Detail.cfm?ID=100 |date=2008-02-15 }}

⚫ == References ==
⚫ *
*Synthesis: ''Organic Syntheses'', Coll. Vol. 5, p.1120 (1973); Vol. 40, p.105 (1960).


{{PAHs}} {{PAHs}}


] ]
]

]
]
]
]

Latest revision as of 01:37, 9 March 2024

Triphenylene
Skeletal formula with numbering convention
Ball-and-stick model
Names
Preferred IUPAC name Triphenylene
Other names Benzophenanthrene
9,10-Benzophenanthrene
1,2,3,4-Dibenzonaphthalene
Isochrysene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.385 Edit this at Wikidata
EC Number
  • 205-922-9
KEGG
MeSH C009590
PubChem CID
UNII
CompTox Dashboard (EPA)
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/h1-12HKey: 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
Appearance white
Density 1.308 g/cm
Melting point 198 °C; 388 °F; 471 K
Boiling point 438 °C; 820 °F; 711 K
Magnetic susceptibility (χ) -156.6·10 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Preparation

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

Properties

Triphenylene is more resonance stable than its isomers chrysene, benzanthracene, benzophenanthrene, and tetracene. For this reason triphenylene resists hydrogenation.

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

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. 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

External links

Polycyclic aromatic hydrocarbons
2 rings
3 rings
4 rings
5 rings
6 rings
7+ rings
General classes
Categories: