Phenacene

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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]PhenaceneCommon nameStructure
[4]phenacene Chrysene Chyrsene horizontal.svg
[5]phenacene Picene Picene horizontal.svg
[6]phenaceneFulminene 6-phenacene.svg
[7]phenacene 7-phenacene.svg

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]

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<span class="mw-page-title-main">Organic electronics</span> Field of materials science

Organic electronics is a field of materials science concerning the design, synthesis, characterization, and application of organic molecules or polymers that show desirable electronic properties such as conductivity. Unlike conventional inorganic conductors and semiconductors, organic electronic materials are constructed from organic (carbon-based) molecules or polymers using synthetic strategies developed in the context of organic chemistry and polymer chemistry.

<span class="mw-page-title-main">Transistor</span> Solid-state electrically operated switch also used as an amplifier

A transistor is a semiconductor device used to amplify or switch electrical signals and power. It is one of the basic building blocks of modern electronics. It is composed of semiconductor material, usually with at least three terminals for connection to an electronic circuit. A voltage or current applied to one pair of the transistor's terminals controls the current through another pair of terminals. Because the controlled (output) power can be higher than the controlling (input) power, a transistor can amplify a signal. Some transistors are packaged individually, but many more in miniature form are found embedded in integrated circuits. Because transistors are the key active components in practically all modern electronics, many people consider them one of the 20th century's greatest inventions.

The Schön scandal concerns German physicist Jan Hendrik Schön who briefly rose to prominence after a series of apparently successful experiments with semiconductors that were discovered later to be fraudulent. Before he was exposed, Schön had received the Otto-Klung-Weberbank Prize for Physics and the Braunschweig Prize in 2001, as well as the Outstanding Young Investigator Award of the Materials Research Society in 2002, all of which were later rescinded. He was also supposed to receive the William L. McMillan Award from the University of Illinois in 2002, but due to the intervention of Daniel C. Ralph of Cornell University, Schön was never given the award.

<span class="mw-page-title-main">Phenanthrene</span> Polycyclic aromatic hydrocarbon composed of three fused benzene rings

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, explosives, and drugs. It has also been used to make bile acids, cholesterol and steroids.

<span class="mw-page-title-main">Conductive polymer</span> Organic polymers that conduct electricity

Conductive polymers or, more precisely, intrinsically conducting polymers (ICPs) are organic polymers that conduct electricity. Such compounds may have metallic conductivity or can be semiconductors. The main advantage of conductive polymers is that they are easy to process, mainly by dispersion. Conductive polymers are generally not thermoplastics, i.e., they are not thermoformable. But, like insulating polymers, they are organic materials. They can offer high electrical conductivity but do not show similar mechanical properties to other commercially available polymers. The electrical properties can be fine-tuned using the methods of organic synthesis and by advanced dispersion techniques.

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<span class="mw-page-title-main">Organic field-effect transistor</span> Type of field-effect transistor

An organic field-effect transistor (OFET) is a field-effect transistor using an organic semiconductor in its channel. OFETs can be prepared either by vacuum evaporation of small molecules, by solution-casting of polymers or small molecules, or by mechanical transfer of a peeled single-crystalline organic layer onto a substrate. These devices have been developed to realize low-cost, large-area electronic products and biodegradable electronics. OFETs have been fabricated with various device geometries. The most commonly used device geometry is bottom gate with top drain and source electrodes, because this geometry is similar to the thin-film silicon transistor (TFT) using thermally grown SiO2 as gate dielectric. Organic polymers, such as poly(methyl-methacrylate) (PMMA), can also be used as dielectric. One of the benefits of OFETs, especially compared with inorganic TFTs, is their unprecedented physical flexibility, which leads to biocompatible applications, for instance in the future health care industry of personalized biomedicines and bioelectronics.

<span class="mw-page-title-main">Pentacene</span> Hydrocarbon compound (C22H14) made of 5 fused benzene rings

Pentacene is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light.

<span class="mw-page-title-main">Rubrene</span> Chemical compound

Rubrene (5,6,11,12-tetraphenyltetracene) is the organic compound with the formula (C18H84. It is a red colored polycyclic aromatic hydrocarbon. Because of its distinctive optical and electrical properties, rubrene has been extensively studied. It has been used as a sensitiser in chemoluminescence and as a yellow light source in lightsticks.

<span class="mw-page-title-main">Tetracene</span> Chemical compound

Tetracene, also called naphthacene, is a polycyclic aromatic hydrocarbon. It has the appearance of a pale orange powder. Tetracene is the four-ringed member of the series of acenes.

<span class="mw-page-title-main">Idrialite</span>

Idrialite is a rare hydrocarbon mineral with approximate chemical formula C22H14.

<span class="mw-page-title-main">Heptacene</span> Chemical compound

Heptacene is an organic compound and a polycyclic aromatic hydrocarbon and the seventh member of the acene or polyacene family of linear fused benzene rings. This compound has long been pursued by chemists because of its potential interest in electronic applications and was first synthesized but not cleanly isolated in 2006. Heptacene was finally fully characterized in bulk by researchers in Germany and the United States in 2017.

<span class="mw-page-title-main">Acene</span> Class of chemical compounds

In organic chemistry, the acenes or polyacenes are a class of organic compounds and polycyclic aromatic hydrocarbons made up of benzene rings which have been linearly fused. They follow the general molecular formula C4n+2H2n+4.

<span class="mw-page-title-main">Printed electronics</span> Electronic devices created by various printing methods

Printed electronics is a set of printing methods used to create electrical devices on various substrates. Printing typically uses common printing equipment suitable for defining patterns on material, such as screen printing, flexography, gravure, offset lithography, and inkjet. By electronic-industry standards, these are low-cost processes. Electrically functional electronic or optical inks are deposited on the substrate, creating active or passive devices, such as thin film transistors; capacitors; coils; resistors. Some researchers expect printed electronics to facilitate widespread, very low-cost, low-performance electronics for applications such as flexible displays, smart labels, decorative and animated posters, and active clothing that do not require high performance.

<span class="mw-page-title-main">Diindenoperylene</span> Chemical compound

Diindenoperylene (DIP) is an organic semiconductor which receives attention because of its potential application in optoelectronics (solar cells, OLEDs) and electronics (RFID tags). DIP is a planar perylene derivative with two indeno-groups attached to opposite sides of the perylene core. Its chemical formula is C32H16, the full chemical name is diindeno[1,2,3-cd:1',2',3'-lm]perylene. Its chemical synthesis has been described.

<span class="mw-page-title-main">Perfluoropentacene</span> Chemical compound

Perfluoropentacene (PFP) is an n-type organic semiconductor, which is made by fluorination of the p-type semiconductor pentacene. It has a blueish-black color, and is used for molecular thin-film devices.

<span class="mw-page-title-main">Rylene dye</span> Dye based on the rylene framework of naphthalene units

A rylene dye is a dye based on the rylene framework of naphthalene units linked in peri-positions. In homologues additional naphthalene units are added, forming compounds — or poly(peri-naphthalene)s — such as perylene, terrylene and quarterrylene.

Low-temperature polycrystalline silicon (LTPS) is polycrystalline silicon that has been synthesized at relatively low temperatures compared to traditional methods. LTPS is important for display industries, since the use of large glass panels prohibits exposure to deformative high temperatures. More specifically, the use of polycrystalline silicon in thin-film transistors (LTPS-TFT) has high potential for large-scale production of electronic devices like flat panel LCD displays or image sensors.

<span class="mw-page-title-main">Bio-FET</span> Type of field-effect transistor

A field-effect transistor-based biosensor, also known as a biosensor field-effect transistor, field-effect biosensor (FEB), or biosensor MOSFET, is a field-effect transistor that is gated by changes in the surface potential induced by the binding of molecules. When charged molecules, such as biomolecules, bind to the FET gate, which is usually a dielectric material, they can change the charge distribution of the underlying semiconductor material resulting in a change in conductance of the FET channel. A Bio-FET consists of two main compartments: one is the biological recognition element and the other is the field-effect transistor. The BioFET structure is largely based on the ion-sensitive field-effect transistor (ISFET), a type of metal–oxide–semiconductor field-effect transistor (MOSFET) where the metal gate is replaced by an ion-sensitive membrane, electrolyte solution, and reference electrode.

<span class="mw-page-title-main">Contorted aromatics</span> Hydrocarbon compounds composed of rings fused such that the molecule is nonplanar

In organic chemistry, contorted aromatics, or more precisely contorted polycyclic aromatic hydrocarbons, are polycyclic aromatic hydrocarbons (PAHs) in which the fused aromatic molecules deviate from the usual planarity.

References

  1. Yamashita, Yoshiro (2009). "Organic semiconductors for organic field-effect transistors". Science and Technology of Advanced Materials. 10 (2): 024313. Bibcode:2009STAdM..10b4313Y. doi:10.1088/1468-6996/10/2/024313. ISSN   1468-6996. PMC   5090443 . PMID   27877286.
  2. Komura, N.; Goto, H.; He, X.; Mitamura, H.; Eguchi, R.; Kaji, Y.; Okamoto, H.; Sugawara, Y.; Gohda, S.; Sato, K.; Kubozono, Y. (2012). "Characteristics of [6]phenacene thin film field-effect transistor". Appl. Phys. Lett. 101 (8): 083301. Bibcode:2012ApPhL.101h3301K. doi:10.1063/1.4747201.
  3. 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. 1 2 Mitsuhashi, R.; Suzuki, Y.; Yamanari, Y.; Mitamura, H.; Kambe, T.; Ikeda, N.; Okamoto, H.; Fujiwara, A.; Yamaji, M.; Kawasaki, N.; Maniwa, Y.; Kubozono, Y. (2010). "Superconductivity in alkali-metal-doped picene". Nature. 464 (7285): 76–79. Bibcode:2010Natur.464...76M. doi:10.1038/nature08859. PMID   20203605.
  5. 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.
  6. Nakano, Y.; Saito, M.; Nakamura, H. WO 2010016511 A1 20100211[ clarify ], 2010.