Picene
Encyclopedia
Picene is a hydrocarbon
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....

 found in the pitch
Pitch (resin)
Pitch is the name for any of a number of viscoelastic, solid polymers. Pitch can be made from petroleum products or plants. Petroleum-derived pitch is also called bitumen. Pitch produced from plants is also known as resin. Products made from plant resin are also known as rosin.Pitch was...

y residue obtained in the distillation
Distillation
Distillation is a method of separating mixtures based on differences in volatilities of components in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....

 of peat
Peat
Peat is an accumulation of partially decayed vegetation matter or histosol. Peat forms in wetland bogs, moors, muskegs, pocosins, mires, and peat swamp forests. Peat is harvested as an important source of fuel in certain parts of the world...

 tar
Tar
Tar is modified pitch produced primarily from the wood and roots of pine by destructive distillation under pyrolysis. Production and trade in tar was a major contributor in the economies of Northern Europe and Colonial America. Its main use was in preserving wooden vessels against rot. The largest...

 and of petroleum
Petroleum
Petroleum or crude oil is a naturally occurring, flammable liquid consisting of a complex mixture of hydrocarbons of various molecular weights and other liquid organic compounds, that are found in geologic formations beneath the Earth's surface. Petroleum is recovered mostly through oil drilling...

. This is distilled to dryness and the distillate repeatedly recrystallize
Recrystallization (chemistry)
-Chemistry:In chemistry, recrystallization is a procedure for purifying compounds. The most typical situation is that a desired "compound A" is contaminated by a small amount of "impurity B". There are various methods of purification that may be attempted , which includes recrystallization...

d from cymene
Cymene
Cymene, or p-cymene, is a naturally occurring aromatic organic compound. It is classified as a hydrocarbon related to a monoterpene. Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group...

. It may be synthetically prepared by the action of anhydrous
Anhydrous
As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another...

 aluminium chloride
Aluminium chloride
Aluminium chloride is the main compound of aluminium and chlorine. It is white, but samples are often contaminated with iron trichloride, giving it a yellow colour. The solid has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large...

 on a mixture of naphthalene
Naphthalene
Naphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...

 and 1,2-dibromoethane
1,2-Dibromoethane
1,2-Dibromoethane, also known as ethylene dibromide , is the chemical compound with the formula BrCH2CH2Br. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly a synthetic...

, or by distilling a-dinaphthostilbene. It crystallizes in large colorless plates which possess a blue fluorescence
Fluorescence
Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation of a different wavelength. It is a form of luminescence. In most cases, emitted light has a longer wavelength, and therefore lower energy, than the absorbed radiation...

. It is soluble in concentrated sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...

 with a green color. Chromic acid
Chromic acid
The term chromic acid is usually used for a mixture made by adding concentrated sulfuric acid to a dichromate, which may contain a variety of compounds, including solid chromium trioxide. This kind of chromic acid may be used as a cleaning mixture for glass. Chromic acid may also refer to the...

 in glacial acetic acid solution oxidizes it to picene-quinone
Quinone
A quinone is a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C– groups with any necessary rearrangement of double bonds," resulting in "a fully conjugated cyclic dione structure."...

, picene-quinone carboxylic acid
Carboxylic acid
Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

, and finally to phthalic acid
Phthalic acid
Phthalic acid is an aromatic dicarboxylic acid, with formula C6H42. It is an isomer of isophthalic acid and terephthalic acid. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large...

.

When intercalated
Intercalation (chemistry)
In chemistry, intercalation is the reversible inclusion of a molecule between two other molecules . Examples include DNA intercalation and graphite intercalation compounds.- DNA intercalation :...

 with potassium
Potassium
Potassium is the chemical element with the symbol K and atomic number 19. Elemental potassium is a soft silvery-white alkali metal that oxidizes rapidly in air and is very reactive with water, generating sufficient heat to ignite the hydrogen emitted in the reaction.Potassium and sodium are...

 or rubidium
Rubidium
Rubidium is a chemical element with the symbol Rb and atomic number 37. Rubidium is a soft, silvery-white metallic element of the alkali metal group. Its atomic mass is 85.4678. Elemental rubidium is highly reactive, with properties similar to those of other elements in group 1, such as very rapid...

and cooled to below 18 K, picene has been shown to exhibit superconductive properties.
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