Chemistry:Phenacene
Phenacenes are a class of organic compounds consisting of fused aromatic rings. They are polycyclic aromatic hydrocarbons, related to acenes and helicenes from which they differ by the arrangement of the fused rings.
| [n]Phenacene | Common name | Molecular formula | Structural formula |
|---|---|---|---|
| [3]Phenacene | Phenanthrene | C 14H 10 |
120px |
| [4]Phenacene | Chrysene | C 18H 12 |
160px |
| [5]Phenacene | Picene | C 22H 14 |
200px |
| [6]Phenacene | Fulminene | C 26H 16 |
240px |
| [7]Phenacene | C 30H 18 |
280px |
Relevance to organic electronic materials
Aromatic compounds with extended π-conjugated system have attracted attention because of their potential use in organic electronics as organic semiconductors.[1] Of academic interest, pentacene has been widely used as an active layer in organic thin-film field-effect transistors (OFET). The main drawback of pentacene OFET is degradation upon exposure to light and air. On the other hand, [n]phenacenes, an isomeric form of [n]acenes, has been known as a stable compound in which the benzene rings are fused in a zigzag structure. For the past several years, there is renewed interest in synthesis of [n]phenacene derivatives associated with electronic applications in emissive and semi- or superconducting materials.[2][3][4]
Picene ([5]phenacene) can serve as an active layer of a high-performance p-channel organic thin-film FET with very high field-effect mobility μ = 5 cm2/(V⋅s).[5] [7]Phenacene FET shows μ = 0.75 cm2/(V⋅s) and no sensitivity to air. Furthermore, picene doped with potassium and rubidium exhibit superconductivity with a maximum critical temperature TC ≈ 18 K.[4] Thus, [n]phenacenes and their derivatives may play an important role in future fabrication of stable and high-performance electronic devices such as OFET, OLED and organic solar cells. Substituted picenes may serve as an active layer of OFETs.[6]
References
- ↑ Yamashita, Yoshiro (2009). "Organic semiconductors for organic field-effect transistors". Science and Technology of Advanced Materials 10 (2). doi:10.1088/1468-6996/10/2/024313. ISSN 1468-6996. PMID 27877286. Bibcode: 2009STAdM..10b4313Y.
- ↑ Komura, N.; Goto, H.; He, X.; Mitamura, H.; Eguchi, R.; Kaji, Y.; Okamoto, H.; Sugawara, Y. et al. (2012). "Characteristics of [6]phenacene thin film field-effect transistor". Appl. Phys. Lett. 101 (8): 083301. doi:10.1063/1.4747201. Bibcode: 2012ApPhL.101h3301K.
- ↑ Ionkin, A. S.; Marshall, W. J.; Fish, B. M.; Bryman, L. M.; Wang, Y. (2008). "A tetra-substituted chrysene: orientation of multiple electrophilic substitution and use of a tetra-substituted chrysene as a blue emitter for OLEDs". Chem. Commun. (20): 2319. doi:10.1039/b715386d.
- ↑ 4.0 4.1 Mitsuhashi, R.; Suzuki, Y.; Yamanari, Y.; Mitamura, H.; Kambe, T.; Ikeda, N.; Okamoto, H.; Fujiwara, A. et al. (2010). "Superconductivity in alkali-metal-doped picene". Nature 464 (7285): 76–79. doi:10.1038/nature08859. PMID 20203605. Bibcode: 2010Natur.464...76M.
- ↑ Okamoto, H.; Kawasaki, N.; Kaji, Y.; Kubozono, Y.; Fujiwara, A.; Yamaji, M. (2008). "Air-assisted high-performance field-effect transistor with thin films of picene". J. Am. Chem. Soc. 130 (32): 10470–10471. doi:10.1021/ja803291a. PMID 18627146.
- ↑ Nakano, Y.; Saito, M.; Nakamura, H. , 2010.
 |  |
