Acene
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 | 
|
| Anthracene | C14H10 | 3 | 178.23 g mol−1 | 120-12-7 | 
|
| Tetracene | C18H12 | 4 | 228.29 g mol−1 | 92-24-0 | 220px |
| Pentacene | C22H14 | 5 | 278.35 g mol−1 | 135-48-8 | 
|
| Hexacene | C26H16 | 6 | 328.41 g mol−1 | 258-31-1 | 
|
| Heptacene | C30H18 | 7 | 378.46 g mol−1 | 258-38-8 | 
|
| 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
- ↑ 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.
- ↑ 2.0 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.
- ↑ 3.0 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.
- ↑ 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.
- ↑ 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.
- ↑ 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>.
- ↑ 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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