Hexacene

Names
Preferred IUPAC name Hexacene
Identifiers
CAS Number	258-31-1 Y
3D model (JSmol)	Interactive image
ChemSpider	109666 N
PubChemCID	123044
CompTox Dashboard(EPA)	DTXSID00180457
InChI InChI=1S/C26H16/c1-2-6-18-10-22-14-26-16-24-12-20-8-4-3-7-19(20)11-23(24)15-25(26)13-21(22)9-17(18)5-1/h1-16H N Key: QSQIGGCOCHABAP-UHFFFAOYSA-N N InChI=1/C26H16/c1-2-6-18-10-22-14-26-16-24-12-20-8-4-3-7-19(20)11-23(24)15-25(26)13-21(22)9-17(18)5-1/h1-16H Key: QSQIGGCOCHABAP-UHFFFAOYAG
SMILES c1c2cc3cc4cc5cc6ccccc6cc5cc4cc3cc2ccc1
Properties
Chemical formula	C26H16
Molar mass	328.41 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Hexacene is anaromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility.^[1]

Hexacene is one of a series of linear polycyclic molecules created by such aromatic ring fusions, a series termedacenes; the previous in the series ispentacene (with five fused rings) and the next isheptacene (with seven). It and other acenes and their derivatives have been investigated in potential applications related toorganic semiconductors. Like larger acenes, hexacene is poorly soluble, but derivatives have been prepared with improved solubility, such as 6,15-Bis(tri-t-butylsilylethynyl)hexacene, which melts with decomposition at 96 °C.^[2]

Hexacene has been the subject of many syntheses. One route uses thermaldecarbonylation of a monoketone precursor.^[1]

• First synthesis:
  • Marschalk, C. Linear hexacenes. Bull. Soc. Chim. Fr. 6, 1112–1121 (1939).
  • E. Clar (1939). "Hexacen, ein grüner, einfacher Kohlenwasserstoff (Aromatische Kohlenwasserstoffe, XXIV. Mitteil) (trans=Hexacene, a Green Simple Hydrocarbon (Aromatic hydrocarbons. XXIV.)".Ber. Dtsch. Chem. Ges. B.72B:1817–1821.doi:10.1002/cber.19390721002.
  • E. Clar (1942). "Eine neue Synthese des Hexacens (Aromatische Kohlenwasserstoffe, XXXIV. Mitteil)".Berichte der deutschen chemischen Gesellschaft.75 (11):1283–1287.doi:10.1002/cber.19420751102.
• Bydehydrogenation ofhexacosahydrohexacene bypalladium on carbonBailey, W.J.; Liao, C.W. (1955). "Cyclic Dienes. XI. New Syntheses of Hexacene and Heptacene".J. Am. Chem. Soc.77 (4):992–993.doi:10.1021/ja01609a055.
• Isolation:Angliker H.; Rommel E.; Wirz J. (1982). "Electronic spectra of hexacene in solution (ground state, triplet state, dication and dianion)".Chemical Physics Letters.87 (2):208–12.Bibcode:1982CPL....87..208A.doi:10.1016/0009-2614(82)83589-6.
• By decarbonylation of adiketone precursor:Mondal, R.; Adhikari, R.M.; Shah, B.K.; Neckers, D.C. (2007). "Revisiting the Stability of Hexacenes".Org. Lett.9 (13):2505–2508.doi:10.1021/ol0709376.PMID 17516652.
• Deoxygenation route:Krüger, Justus; Eisenhut, Frank; Alonso, José M.; Lehmann, Thomas; Guitián, Enrique; Pérez, Dolores; Skidin, Dmitry; Gamaleja, Florian; Ryndyk, Dmitry A.; Joachim, Christian; Peña, Diego; Moresco, Francesca; Cuniberti, Gianaurelio (2017). "Imaging the electronic structure of on-surface generated hexacene".Chem. Commun.53 (10):1583–1586.doi:10.1039/C6CC09327B.ISSN 1359-7345.PMID 27990553.

• Molecular graphics representation of the X-ray crystallographic structure determined for 6,15-bis(tri-t-butylsilylethynyl)hexacene—hexacene with bulky, protective substituents in the reactive 6- and 15- ring positions, see rotating graphic at base of page.
• Sander-Wise Polycyclic Aromatic Hydrocarbon Structure Index entry for hexacene, NIST Special Publication 922.

• Organic semiconductors
• Acenes
• Polycyclic aromatic hydrocarbons
• Hexacyclic compounds

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