Phenacene
{{short description|Group of chemical compounds}}
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.
| class="wikitable" |
| [n]Phenacene
! Common name ! Structure |
|---|
| [4]phenacene
| Chrysene | 170px |
| [5]phenacene
| Picene | 205px |
| [6]phenacene
| Fulminene | 240px |
| [7]phenacene
| | 275px |
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.{{cite journal |last1=Yamashita |first1=Yoshiro |title=Organic semiconductors for organic field-effect transistors |journal=Science and Technology of Advanced Materials |volume=10 |issue=2 |year=2009 |pages=024313 |issn=1468-6996 |doi=10.1088/1468-6996/10/2/024313 |pmc=5090443 |pmid=27877286 |bibcode=2009STAdM..10b4313Y}}
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.{{cite journal |author1=Komura, N. |author2=Goto, H. |author3=He, X. |author4=Mitamura, H. |author5=Eguchi, R. |author6=Kaji, Y. |author7=Okamoto, H. |author8=Sugawara, Y. |author9=Gohda, S. |author10=Sato, K. |author11=Kubozono, Y. | title = Characteristics of [6]phenacene thin film field-effect transistor | journal = Appl. Phys. Lett. | date = 2012 | volume = 101 | issue = 8 | pages = 083301 | doi = 10.1063/1.4747201| bibcode = 2012ApPhL.101h3301K }}{{cite journal |author1=Ionkin, A. S. |author2=Marshall, W. J. |author3=Fish, B. M. |author4=Bryman, L. M. |author5=Wang, Y. | journal = Chem. Commun. | date = 2008 | pages = 2319 | doi = 10.1039/b715386d | title=A tetra-substituted chrysene: orientation of multiple electrophilic substitution and use of a tetra-substituted chrysene as a blue emitter for OLEDs | issue=20}}{{cite journal |author1=Mitsuhashi, R. |author2=Suzuki, Y. |author3=Yamanari, Y. |author4=Mitamura, H. |author5=Kambe, T. |author6=Ikeda, N. |author7=Okamoto, H. |author8=Fujiwara, A. |author9=Yamaji, M. |author10=Kawasaki, N. |author11=Maniwa, Y. |author12=Kubozono, Y. | title = Superconductivity in alkali-metal-doped picene | journal = Nature | date = 2010 | volume = 464 | issue = 7285 | pages = 76–79 |doi=10.1038/nature08859 | pmid = 20203605 | bibcode = 2010Natur.464...76M }}
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).{{cite journal |author1=Okamoto, H. |author2=Kawasaki, N. |author3=Kaji, Y. |author4=Kubozono, Y. |author5=Fujiwara, A. |author6=Yamaji, M. | title = Air-assisted high-performance field-effect transistor with thin films of picene | journal = J. Am. Chem. Soc. | date = 2008 | volume = 130| issue = 32 | pages = 10470–10471 | pmid = 18627146 | doi = 10.1021/ja803291a }} [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. 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.Nakano, Y.; Saito, M.; Nakamura, H. {{clarify span|WO 2010016511 A1 20100211|date=February 2024}}, 2010.
References
{{reflist|30em}}{{PAHs}}