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Acene
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 . 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. The first 5 unsubstituted members are listed in the following table: Hexacene is not stable in air, and dimerises upon isolation. Heptacene (and larger acenes) is very reactive and has only been isolated in a matrix. However, bis(trialkylsilylethynylated) versions of heptacene have been isolated as crystalline solids. Larger acenes Due to their increased conjugation length the larger acenes are also studied. Theoretically, a number of reports are available on longer chains ...
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Pentacene 200
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. Structurally, pentacene is one of the linear acenes, the previous one being tetracene (four fused benzene rings) and the next one being hexacene (six fused benzene rings). In August 2009, a group of researchers from IBM published experimental results of imaging a single molecule of pentacene using an atomic force microscope. In July 2011, they used a modification of scanning tunneling microscopy to experimentally determine the shapes of the highest occupied and lowest unoccupied molecular orbitals. In 2012, pentacene-doped ''p''-terphenyl was shown to be effective as the amplifi ...
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Pentacene
Pentacene () is a polycyclic aromatic hydrocarbon A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ... consisting of five linearly-fused benzene () Ring (chemistry), rings. This highly Conjugation (organic chemistry), 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 Chemical decomposition, degrades upon exposure to air and light. Structurally, pentacene is one of the linear acenes, the previous one being tetracene (four fused benzene rings) and the next one being hexacene (six fused benzene rings). In August 2009, a group of researchers from IBM published experimental results of imaging a sin ...
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Anthracene
Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation. Occurrence and production Coal tar, which contains around 1.5% anthracene, remains a major source of this material. Common impurities are phenanthrene and carbazole. The mineral form of anthracene is called freitalite and is related to a coal deposit. A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction, for example from ''o''-tolyl phenyl ketone. Reactions Reduction Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+ nthracenesup>− (M = Li, Na, K). Hydrogenation gives 9,10- dihydroant ...
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Acenes General Structure
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 . 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. The first 5 unsubstituted members are listed in the following table: Hexacene is not stable in air, and dimerises upon isolation. Heptacene (and larger acenes) is very reactive and has only been isolated in a matrix. However, bis(trialkylsilylethynylated) versions of heptacene have been isolated as crystalline solids. Larger acenes Due to their increased conjugation length the larger acenes are also studied. Theoretically, a number of reports are available on longer chains us ...
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Heptacene 200
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. : The final step is a photochemical decarbonylization with a 1,2-dione bridge extruded as carbon monoxide. In solution heptacene is not formed because it is very unstable being a reactive DA diene and quickly reacts with oxygen or forms dimers. When on the other hand the dione precursor is dissolved in a PMMA matrix first, heptacene can be studied by spectroscopy. Heptacene has been studied spectroscopically at cryogenic temperatures in a matrix. When dissolved in sulfuric acid the heptacene dication is reported to be stable at room-temperature for more ...
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Heptacene
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. : The final step is a photochemical decarbonylization with a 1,2-dione bridge extruded as carbon monoxide. In solution heptacene is not formed because it is very unstable being a reactive DA diene and quickly reacts with oxygen or forms dimers. When on the other hand the dione precursor is dissolved in a PMMA matrix first, heptacene can be studied by spectroscopy. Heptacene has been studied spectroscopically at cryogenic temperatures in a matrix. When dissolved in sulfuric acid the heptacene dication is reported to be stable at room-temperature for more ...
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Hexacene 200
Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility. Hexacene 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 (with five fused rings) and the next being heptacene (with seven). It and other acenes and their derivatives have been investigated in potential applications related to organic semiconductors. Like larger acenes, hexacene is poorly soluble, but derivatives have been prepared with improved solubility. 6,15-Bis(tri-t-butylsilylethynyl)hexacene, which melts with decomposition at 96 °C. Syntheses and structure Hexacene has been the subject of many syntheses. One route entails by thermal decarbonylation of monoketone precursor. Further reading *First synthesis: **Marschalk, C. Linear hexacenes. Bull. Soc. Chim. Fr. 6, 1112–1121 (1939). ** ** *By dehydrogenation of ''hexacos ...
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Hexacene
Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility. Hexacene 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 (with five fused rings) and the next being heptacene (with seven). It and other acenes and their derivatives have been investigated in potential applications related to organic semiconductors. Like larger acenes, hexacene is poorly soluble, but derivatives have been prepared with improved solubility. 6,15-Bis(tri-t-butylsilylethynyl)hexacene, which melts with decomposition at 96 °C. Syntheses and structure Hexacene has been the subject of many syntheses. One route entails by thermal decarbonylation of monoketone precursor. Further reading *First synthesis: **Marschalk, C. Linear hexacenes. Bull. Soc. Chim. Fr. 6, 1112–1121 (1939). ** ** *By dehydrogenation of ''hexacosa ...
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Polycyclic Aromatic Hydrocarbon
A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. PAHs are uncharged, non-polar and planar. Many are colorless. Many of them are found in coal and in oil deposits, and are also produced by the combustion of organic matter—for example, in engines and incinerators or when biomass burns in forest fires. Polycyclic aromatic hydrocarbons are discussed as possible starting materials for abiotic syntheses of materials required by the earliest forms of life. Nomenclature and structure The terms polyaromatic hydrocarbon or polynuclear aromatic hydrocarbon are also used for this concept. By definition, polycyclic aromatic hydrocarbons have multiple rings, precluding benzene from being considered a PAH. Some sources, such as the US EPA and CDC, consider naphthalene to be the simplest PAH. ...
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Tetracene 200
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. Jan Hendrik Schön during his time at Bell Labs (1997–2002) claimed to have developed an electrically pumped laser based on tetracene. However, his results could not be reproduced, and this is considered to be a scientific fraud. Napthacene is the main ...
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Tetracene
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. Jan Hendrik Schön during his time at Bell Labs (1997–2002) claimed to have developed an electrically pumped laser based on tetracene. However, his results could not be reproduced, and this is considered to be a scientific fraud. Napthacene is the ...
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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 f ...
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