Acene

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The general structural formula for acenes

Acenes (sometimes referred to as polyacenes) form a functional class of organic compounds: they are polycyclic aromatic hydrocarbons made up of linearly fused benzene rings.[1] The larger acenes have potential interest in optoelectronic applications and as organic semiconductors.[2][3] Pentacene has been incorporated into organic field-effect transistors, reaching charge carrier mobilities as high as 5 cm2 V−1 s−1.[2] Unsubstituted acenes larger than pentacene have only been studied by matrix isolation techniques,[2][3][4] although substituted acenes up to nonacene have been isolated.[2][5]

Name Molecular
formula
Number
of rings
Molar mass CAS
number
Structural formula
Naphthalene C10H8 2 128.17 g mol−1 91-20-3 Naphthalene-2D-Skeletal.svg
Anthracene C14H10 3 178.23 g mol−1 120-12-7 Anthracene-2D-Skeletal.png
Tetracene C18H12 4 228.29 g mol−1 92-24-0 220px
Pentacene C22H14 5 278.35 g mol−1 135-48-8 Pentacene.svg
Hexacene C26H16 6 328.41 g mol−1 258-31-1 Hexacene.svg
Heptacene C30H18 7 378.46 g mol−1 258-38-8 Heptaceen.png
Octacene C34H20 8 428.52 g mol−1 258-33-3
Nonacene C38H22 9 478.58 g mol−1

Nomenclature

Napthalene and anthracene have retained names.[6] Other acenes are named by a numerical prefix followed by the suffix "-acene", although tetracene also has the trivial name "naphthacene".[7]

Related compounds

A related group of compounds with 1,2-fused rings and with helical not linear structures are the helicenes. Polyquinanes and quinenes are fused cyclopentane rings.

References

  1. Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995). Pure Appl. Chem. 1995, 67 (8-9), 1307–75 at 1310. DOI: 10.1351/pac199567081307.
  2. 2.0 2.1 2.2 2.3 Anthony, John  E. The Larger Acenes: Versatile Organic Semiconductors. Angew. Chem., Int. Ed. Engl. 2008, 47 (3), 452–83. DOI: 10.1002/anie.200604045.
  3. 3.0 3.1 Zade, Sanjio S.; Bendikov, Michael Heptacene and Beyond: the Longest Characterized Acenes. Angew. Chem., Int. Ed. Engl. 2010, 49 (24), 1012–15. DOI: 10.1002/anie.200906002.
  4. Tönshoff, Christina; Bettinger, Holger F. Photogeneration of Octacene and Nonacene. Angew. Chem. Int. Ed. Engl. 2010, 49 (24), 4125–28. DOI: 10.1002/anie.200906355.
  5. Kaur, Irvinder; Jazdzyk, Mikael; Stein, Nathan N.; Prusevich, Polina; Miller, Glen P. Design, Synthesis, and Characterization of a Persistent Nonacene Derivative. J. Am. Chem. Soc. 2010, 132 (4), 1261–63. DOI: 10.1021/ja9095472.
  6. A Guide to IUPAC Nomenclature of Organic Compounds; IUPAC Recommendations 1993; Blackwell Science: Oxford, 1993; p 164. ISBN 0-632-03488-2, <http://www.acdlabs.com/iupac/nomenclature/93/r93_687.htm>.
  7. Rule A-21. In Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H; IUPAC Recommendations 1979; Pergamon: Oxford, 1979. ISBN 0-08022-369-9, <http://www.acdlabs.com/iupac/nomenclature/79/r79_63.htm>.
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