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| ImageFile = Triphenylene_chemical_structure.png |
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| verifiedrevid = 455515671 |
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| ImageSize = 180px |
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| ImageFile = Triphenylene V2.svg |
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| ImageName = Skeletal formula with numbering convention |
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| ImageSize = 150px |
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| ImageFile1 = Triphenylene-3D-balls.png |
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| ImageName = Skeletal formula with numbering convention |
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| ImageSize1 = 180px |
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| ImageFile1 = Triphenylene-3D-balls.png |
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| ImageName1 = Ball-and-stick model |
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| ImageFile2 = Triphenylene_crystals.jpg |
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| IUPACName = triphenylene |
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| ImageSize1 = 180px |
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| OtherNames = benzophenanthrene, 9,10-benzophenanthrene, 1,2,3,4-dibenznaphthalene, isochrysene |
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| ImageName1 = Ball-and-stick model |
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| Section1 = {{Chembox Identifiers |
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| 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> |
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| CASNo_Ref = {{cascite}} |
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| OtherNames = Benzophenanthrene<br />9,10-Benzophenanthrene<br />1,2,3,4-Dibenzonaphthalene<br />Isochrysene |
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| CASNo = 217-59-4 |
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| Section1 = {{Chembox Identifiers |
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| PubChem = 9170 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| 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 |
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| PubChem = |
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| CASNo = 217-59-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 18WX3373I0 |
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| PubChem = 9170 |
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| 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 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 33080 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1797416 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19541 |
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| KEGG = C19541 |
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| SMILES = C1(C=CC=C3)=C3C(C=CC=C4)=C4C2=C1C=CC=C2 |
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| SMILES = c1(cccc3)c3c(cccc4)c4c2c1cccc2 |
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| MeSHName = C009590 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Section2 = {{Chembox Properties |
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| 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 |
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| C=18|H=12 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| Appearance = |
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| StdInChIKey = SLGBZMMZGDRARJ-UHFFFAOYSA-N |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8816 |
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| EINECS = 205-922-9 |
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| Section2 = {{Chembox Properties |
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| C=18 | H=12 |
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| Appearance = white |
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| 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> |
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| MeltingPtK = 471 |
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| MeltingPtK = 471 |
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| BoilingPtK = 711 |
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| BoilingPtK = 711 |
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| Solubility = }} |
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| MagSus = -156.6·10<sup>−6</sup> cm<sup>3</sup>/mol }} |
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In ], the ] '''triphenylene''' is a flat ] (PAH) consisting of four fused ] rings. Triphenylene can be isolated from ] but 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 C<sub>18</sub>H<sub>12</sub>. |
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'''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. |
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==Preparation== |
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Triphenylene is a fully benzenoid PAH, meaning its structure is composed only of full benzene rings interconnected by carbon-carbon 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. |
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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> |
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== Properties == |
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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 saturated hydrocarbon. |
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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> |
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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> |
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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}} |
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== References == |
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{{reflist}} |
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== External links == |
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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. |
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* {{Webarchive|url=https://web.archive.org/web/20080215085302/http://ois.nist.gov/pah/sp922_Detail.cfm?ID=100 |date=2008-02-15 }} |
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== References == |
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* |
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*Synthesis: ''Organic Syntheses'', Coll. Vol. 5, p.1120 (1973); Vol. 40, p.105 (1960). |
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