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Acene

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Acene

The general structural formula for acenes

The acenes or polyacenes are a class of organic field-effect transistors, reaching charge carrier mobilities as high as 5 cm2/Vs.

The first 7 unsubstituted members are listed in table 1.
Name Molecular formula Number of rings Molar mass CAS number Structural formula
Benzene C6H6 1 78.11 g/mol 71-43-2
Naphthalene C10H8 2 128.17 g/mol 91-20-3
Anthracene C14H10 3 178.23 g/mol 120-12-7
Tetracene C18H12 4 228.29 g/mol 92-24-0
Pentacene C22H14 5 278.35 g/mol 135-48-8
Hexacene C26H16 6 328.41 g/mol 258-31-1
Heptacene C30H18 7 378.46 g/mol 258-38-8

The last members, hexacene and heptacene, are very reactive and have only been isolated in a matrix. However, bis(trialkylsilylethynylated) versions of hexacene and heptacene have been isolated as crystalline solids.[1]

Larger acenes

Due to their increased conjugation length the larger acenes are also studied.[2] They are also building blocks for nanotubes and graphene. Unsubstituted octacene (n=8) and nonacene (n=9) [3] have been detected in matrix isolation. The first reports of stable nonacene derivatives claimed that due to the electronic effects of the thioaryl substituents the compound is not a diradical but a closed-shell compound with the lowest HOMO-LUMO gap reported for any acene,[4] an observation in violation of Kasha's rule. Subsequent work by others on different derivatives included crystal structures, with no such violations.[5]

Related compounds

A related group of compounds with 1,2-fused rings and with helical not linear structures are the helicenes. Compounds in which the fused rings form a zigzag pattern are phenacenes. Polyquinanes and quinenes are fused cyclopentane rings.

References

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