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 utilization in organic electronics. [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 of 5 cm2∙V−1∙s−1. [5] [7]Phenacene FET shows effect mobility μ of 0.75 cm2∙V−1∙s−1 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]

Related Research Articles

Organic electronics Field of materials science researching organic substances with electronic properties

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.

OLED Diode which emits light from an organic compound

An organic light-emitting diode, also known as an organic EL diode, is a light-emitting diode (LED) in which the emissive electroluminescent layer is a film of organic compound that emits light in response to an electric current. This organic layer is situated between two electrodes; typically, at least one of these electrodes is transparent. OLEDs are used to create digital displays in devices such as television screens, computer monitors, portable systems such as smartphones, handheld game consoles and PDAs. A major area of research is the development of white OLED devices for use in solid-state lighting applications.

The Schön scandal concerns German physicist Jan Hendrik Schön who briefly rose to prominence after a series of apparent breakthroughs with semiconductors that were later discovered 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, both of which were later rescinded.

Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in form of molecular crystals or amorphous thin films. In general, they are electrical insulators, but become semiconducting when charges are either injected from appropriate electrodes, upon doping or by photoexcitation.

Organic 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.

Pentacene chemical compound

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.

Rubrene chemical compound

Rubrene (5,6,11,12-tetraphenyltetracene) is a red colored polycyclic aromatic hydrocarbon. Rubrene is used as a sensitiser in chemoluminescence and as a yellow light source in lightsticks.

Tetracene 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. Tetracene is a molecular organic semiconductor, used in organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). In May 2007, researchers from two Japanese universities, Tohoku University in Sendai and Osaka University, reported an ambipolar light-emitting transistor made of a single tetracene crystal. Ambipolar means that the electric charge is transported by both positively charged holes and negatively charged electrons. Tetracene can be also used as a gain medium in dye lasers as a sensitiser in chemoluminescence.

Hexacene chemical compound

Hexacene is an aromatic molecule consisting of six linearly-fused benzene rings. It is one of a series of linear polycyclic molecules created by such aromatic ring fusions, a series termed acenes—the previous in the series being pentacene and the next being heptacene. The CAS registry number for hexacene is 258-38-8, and it has a molecular weight of 328 g/mol. It and other acenes and their derivatives have been investigated in potential applications related to organic semiconductors.

An organic superconductor is a synthetic organic compound that exhibits superconductivity at low temperatures.

Heptacene 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.

Acene class of chemical compounds

The acenes or polyacenes are a class of organic compounds and polycyclic aromatic hydrocarbons made up of linearly fused benzene rings. The larger representatives have potential interest in optoelectronic applications and are actively researched in chemistry and electrical engineering. Pentacene has been incorporated into organic field-effect transistors, reaching charge carrier mobilities as high as 5 cm2/Vs.

Printed electronics

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. Printed electronics is expected 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.

Diindenoperylene 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.

Perfluoropentacene 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.

Silicene two-dimensional allotrope of silicon

Silicene is a two-dimensional allotrope of silicon, with a hexagonal honeycomb structure similar to that of graphene. Contrary to graphene, silicene is not flat, but has a periodically buckled topology; the coupling between layers in silicene is much stronger than in multilayered graphene; and the oxidized form of silicene, 2D silica, has a very different chemical structure from graphene oxide.

Field-effect transistor transistor that uses an electric field to control its electrical behaviour

The field-effect transistor (FET) is a type of transistor which uses an electric field to control the flow of current. FETs are devices with three terminals: source, gate, and drain. FETs control the flow of current by the application of a voltage to the gate, which in turn alters the conductivity between the drain and source.

Potential graphene applications include lightweight, thin, and flexible electric/photonics circuits, solar cells, and various medical, chemical and industrial processes enhanced or enabled by the use of new graphene materials.

Bio-FET

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.

Contorted aromatics

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): 76–9. 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): 10470–1. doi:10.1021/ja803291a. PMID   18627146.
  6. Nakano, Y.; Saito, M.; Nakamura, H. WO 2010016511 A1 20100211, 2010.