Hexacene

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Hexacene
Skeletal formula of hexacene Hexacene.svg
Skeletal formula of hexacene
Hexacene molecule spacefill.png
Names
Preferred IUPAC name
Hexacene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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 X mark.svgN
    Key: QSQIGGCOCHABAP-UHFFFAOYSA-N X mark.svgN
  • 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
  • c1c2cc3cc4cc5cc6ccccc6cc5cc4cc3cc2ccc1
Properties
C26H16
Molar mass 328.41 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility. [1]

Contents

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. [2]

Syntheses and structure

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

Packing diagram of crystalline hexacene, illustrating the herringbone structure. Hexacene(ZZZDKE01).png
Packing diagram of crystalline hexacene, illustrating the herringbone structure.

Further reading

References

  1. 1 2 3 Watanabe, M.; Chang, Y.J.; Liu, S.-W.; Chao, T.-H.; Goto, K.; Islam, M.M.; Yuan, C.H.; Tao, Y.T.; Shinmyozu, T.; Chow, T.J. (2012). "The synthesis, crystal structure and charge-transport properties of hexacene". Nature Chemistry. 4 (7): 574–578. Bibcode:2012NatCh...4..574W. doi:10.1038/nchem.1381. PMID   22717444.
  2. Payne M. M.; Parkin S. R.; Anthony J. E. (2005). "Functionalized higher acenes: hexacene and heptacene". Journal of the American Chemical Society . 127 (22): 8028–9. doi:10.1021/ja051798v. PMID   15926823.