Hexacene
title: "Hexacene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["organic-semiconductors", "acenes", "polycyclic-aromatic-hydrocarbons", "hexacyclic-compounds"] topic_path: "general/organic-semiconductors" source: "https://en.wikipedia.org/wiki/Hexacene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 407811865 | ImageFile = Hexacene.svg | ImageSize = 230px | ImageName = Skeletal formula of hexacene | ImageFile1 = Hexacene molecule spacefill.png | ImageSize1 = 240px | ImageAlt1 = Space-filling-stick model of the hexacene molecule | PIN = Hexacene | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 258-31-1 | PubChem = 123044 | ChemSpiderID_Ref = | ChemSpiderID = 109666 | 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 | InChIKey = QSQIGGCOCHABAP-UHFFFAOYAG | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = QSQIGGCOCHABAP-UHFFFAOYSA-N | SMILES = c1c2cc3cc4cc5cc6ccccc6cc5cc4cc3cc2ccc1 |Section2={{Chembox Properties | Formula = C26H16 | MolarMass = 328.41 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}
Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility.
Hexacene is one of a series of linear polycyclic molecules created by such aromatic ring fusions, a series termed acenes; the previous in the series is pentacene (with five fused rings) and the next is heptacene (with seven). It and other acenes and their derivatives have been investigated in potential applications related to organic 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.{{cite journal |author1=Payne M. M. |author2=Parkin S. R. |author3=Anthony J. E. | title = Functionalized higher acenes: hexacene and heptacene | journal = Journal of the American Chemical Society | year = 2005 | volume = 127 | issue = 22 | pages = 8028–9 | doi = 10.1021/ja051798v | pmid = 15926823 }}
Syntheses and structure
Hexacene has been the subject of many syntheses. One route uses thermal decarbonylation of a monoketone precursor. ::figure[src="https://upload.wikimedia.org/wikipedia/commons/4/4b/Hexacene(ZZZDKE01).png" caption="Packing diagram of crystalline hexacene, illustrating the herringbone structure."] ::
References
References
- (2012). "The synthesis, crystal structure and charge-transport properties of hexacene". Nature Chemistry.
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