Chemistry:Hexacene

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Hexacene
Skeletal formula of hexacene
Space-filling-stick model of the hexacene molecule
Names
Preferred IUPAC name
Hexacene
Identifiers
3D model (JSmol)
ChemSpider
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]

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 being pentacene (with five fused rings) and the next being 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. 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 entails by thermal decarbonylation of monoketone precursor.[1]

Packing diagram of crystalline hexacene, illustrating the herringbone structure.[1]

Further reading

External links

References

  1. 1.0 1.1 1.2 Watanabe, M.; Chang, Y.J.; Liu, S.-W.; Chao, T.-H.; Goto, K.; Islam, M.M.; Yuan, C.H.; Tao, Y.T. et al. (2012). "The synthesis, crystal structure and charge-transport properties of hexacene". Nature Chemistry 4 (7): 574–578. doi:10.1038/nchem.1381. PMID 22717444. Bibcode2012NatCh...4..574W. 
  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.