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. Pentacene has been incorporated into organic field-effect transistors, reaching charge carrier mobilities as high as 5 cm2/Vs. Unsubstituted acenes larger than pentacene have only been studied by matrix isolation techniques, although substituted acenes up to nonacene have been isolated.
| Naam | Molecular formula | Number of rings | Molar mass | CAS number | Structural formula |
|---|---|---|---|---|---|
| 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 | 220px |
| 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 | 
|
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.[2]
Larger acenes
Due to their increased conjugation length the larger acenes are also studied [3]. They are also building blocks for nanotubes and graphene. Unsubstituted octacene (n=8) and nonacene (n=9) [4] have been detected in matrix isolation. A stable substituted nonacene was has also been reported [5]. Due to its array of substituents the compound is not a diradical but a closed-shell compound with the lowest HOMO-LUMO gap reported for any acene.
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.
- ↑ Anthony, John E. The Larger Acenes: Versatile Organic Semiconductors. Angew. Chem., Int. Ed. Engl. 2008, 47 (3), 452–83. DOI: 10.1002/anie.200604045.
- ↑ Zade, Sanjio S.; Bendikov, Michael Heptacene and Beyond: the Longest Characterized Acenes. Angewandte Chemie International Edition 2010, 49 (24), 1012–15. DOI: 10.1002/anie.200906002.
- ↑ Tönshoff, Christina; Bettinger, Holger F. Photogeneration of Octacene and Nonacene. Angewandte Chemie International Edition 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. Journal of the American Chemical Society 2010, 132 (4), 1261–63. DOI: 10.1021/ja9095472.
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