Acene

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The general structural formula for acenes

In

molecular formula
C4n+2H2n+4.

The larger representatives have potential interest in

optoelectronic applications and are actively researched in chemistry and electrical engineering. Pentacene has been incorporated into organic field-effect transistors, reaching charge carrier
mobilities as high as 5 cm2/Vs.

The first 5 unsubstituted members are listed in the following table:

Name Number of rings
Molecular formula
Structural formula
Anthracene 3 C14H10
Tetracene 4 C18H12
Pentacene 5 C22H14
Hexacene 6 C26H16
Heptacene 7 C30H18

Hexacene is not stable in air, and

dimerises upon isolation. Heptacene (and larger acenes) is very reactive and has only been isolated in a matrix. However, bis(trialkylsilylethynylated) versions of heptacene have been isolated as crystalline solids.[3]

Larger acenes

Due to their increased

HOMO-LUMO gap reported for any acene,[8] an observation in violation of Kasha's rule. Subsequent work by others on different derivatives included crystal structures, with no such violations.[9] The on-surface synthesis and characterization of unsubstituted, parent nonacene (n=9)[10] and decacene (n=10)[11] have been reported. In 2020, scientists reported about the creation of dodecacene (n=12)[12] for the first time. Four years later, in the beginning of 2024, Ruan et al. succeeded in synthesizing unsubstitued tridecacene (n=13) on a (111)-gold surface. The acene was characterized by STM- and STS-measurements. [13]

Related compounds

The acene series have the consecutive rings linked in a linear chain, but other chain linkages are possible. The phenacenes have a zig-zag structure and the helicenes have a helical structure.

  • Macromolecular forms consisting of seven fused benzene rings
  • Heptacene
    Heptacene
  • [7]Phenacene
    [7]Phenacene
  • M-heptahelicene
    M-heptahelicene

Benz[a]anthracene, an isomer of tetracene, has three rings connected in a line and one ring connected at an angle.

References

  1. ^ Electronic structure of higher acenes and polyacene: The perspective developed by theoretical analyses Holger F. Bettinger Pure Appl. Chem., Vol. 82, No. 4, pp. 905–915, 2010.
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