Anthracene Photodimerisation
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Anthracene is a solid
polycyclic aromatic hydrocarbon A Polycyclic aromatic hydrocarbon (PAH) is any member of a class of organic compounds that is composed of multiple fused aromatic rings. Most are produced by the incomplete combustion of organic matter— by engine exhaust fumes, tobacco, incine ...
(PAH) of formula C14H10, consisting of three fused
benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
rings. It is a component of
coal tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoria ...
. Anthracene is used in the
production Production may refer to: Economics and business * Production (economics) * Production, the act of manufacturing goods * Production, in the outline of industrial organization, the act of making products (goods and services) * Production as a stat ...
of the red
dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...
alizarin Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula that has been used throughout history as a red dye, principally for dyeing textile fabrics. Historically it wa ...
and other dyes, as a
scintillator A scintillator ( ) is a material that exhibits scintillation, the property of luminescence, when excited by ionizing radiation. Luminescent materials, when struck by an incoming particle, absorb its energy and scintillate (i.e. re-emit the ab ...
to detect high energy particles, as production of pharmaceutical drugs. Anthracene is colorless but exhibits a blue (400–500 nm peak)
fluorescence Fluorescence is one of two kinds of photoluminescence, the emission of light by a substance that has absorbed light or other electromagnetic radiation. When exposed to ultraviolet radiation, many substances will glow (fluoresce) with colore ...
under
ultraviolet Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of ...
radiation.


History and etymology

Crude anthracene (with a melting point of only 180°) was discovered in 1832 by
Jean-Baptiste Dumas Jean Baptiste André Dumas (; 14 July 180010 April 1884) was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights (relative atomic masses) and molecular weights by measuri ...
and
Auguste Laurent Auguste Laurent (14 November 1807 – 15 April 1853) was a French chemist who helped in the founding of organic chemistry with his discoveries of trichloroethylene, anthracene, phthalic acid, and carbolic acid. He devised a systematic nomenc ...
who crystalized it from a fraction of coal tar later known as "anthracene oil". Since their (inaccurate) measurements showed the proportions of carbon and hydrogen of it to be the same as in
naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...
, Laurent called it ''paranaphtaline'' in his 1835 publication of the discovery, which is translated to English as paranaphthalene. Two years later, however, he decided to rename the compound to its modern name derived from because after discovering other polyaromatic hydrocarbons he decided it was only one of isomers of naphthalene. This notion was disproved in 1850s and 1860s.


Occurrence and production

Anthracene, as many other
polycyclic aromatic hydrocarbons A Polycyclic aromatic hydrocarbon (PAH) is any member of a class of organic compounds that is composed of multiple fused aromatic rings. Most are produced by the incomplete combustion of organic matter— by engine exhaust fumes, tobacco, incin ...
, is generated during combustion processes. Most human exposure is through
tobacco smoke Tobacco smoke is a sooty aerosol produced by the incomplete combustion of tobacco during the smoking of cigarettes and other tobacco products. Temperatures in burning cigarettes range from about 400 °C between puffs to about 900 °C ...
or ingestion of charred food. The mineral form of anthracene is called freitalite and is related to a coal deposit. Coal tar, which contains around 1.5% anthracene, remains a major industrial source of this material. Common impurities are
phenanthrene 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, expl ...
and
carbazole Carbazole is an aromatic Heterocyclic compound, heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is ...
. 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- dihydroanthracene, preserving the aromaticity of the two flanking rings.


Cycloadditions

In any solvent except water, anthracene photodimerizes by the action of UV light: : The dimer, called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the +4
cycloaddition In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of th ...
. It reverts to anthracene thermally or with UV irradiation below 300 nm. Substituted anthracene derivatives behave similarly. The reaction is affected by the presence of
oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...
. Anthracene also reacts with dienophile
singlet oxygen Singlet oxygen, systematically named dioxygen(singlet) and dioxidene, is a gaseous inorganic chemistry, inorganic chemical with the formula O=O (also written as or ), which is in a quantum state where all electrons are Radical (chemistry), spin p ...
in a +2cycloaddition (
Diels–Alder reaction In organic chemistry, the Diels–Alder reaction is a chemical reaction between a Conjugated system, conjugated diene and a substituted alkene, commonly termed the Diels–Alder reaction#The dienophile, dienophile, to form a substituted cyclohexe ...
): :


With electrophiles

Chemical
oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
occurs readily, giving
anthraquinone Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic hydrocarbon, aromatic organic compound with formula . Several isomers exist but these terms usually refer to 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein th ...
, C14H8O2 (below), for example using
hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...
and
vanadyl acetylacetonate Vanadyl acetylacetonate is the chemical compound with the chemical formula, formula VO(acac)2, where acac– is the conjugate base of acetylacetone. It is a blue-green solid that dissolves in polar organic solvents. The complex (chemistry), coordin ...
. : Electrophilic substitution of anthracene occurs at the 9 position. For example, formylation affords 9-anthracenecarboxaldehyde. Substitution at other positions is effected indirectly, for example starting with anthroquinone. Bromination of anthracene gives 9,10-dibromoanthracene.


Uses

Anthracene proper has application as an
organic semiconductor 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 the form of molecular crystals o ...
and chemical feedstock for various preservatives and dyes.


Electronics

Anthracene is a wide band-gap
organic semiconductor 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 the form of molecular crystals o ...
, with an
emission spectrum The emission spectrum of a chemical element or chemical compound is the Spectrum (physical sciences), spectrum of frequencies of electromagnetic radiation emitted due to electrons making a atomic electron transition, transition from a high energ ...
peaking between 400 nm and 440 nm. Organic
field-effect transistor The field-effect transistor (FET) is a type of transistor that uses an electric field to control the current through a semiconductor. It comes in two types: junction FET (JFET) and metal-oxide-semiconductor FET (MOSFET). FETs have three termi ...
s have been constructed from it. In
particle physics Particle physics or high-energy physics is the study of Elementary particle, fundamental particles and fundamental interaction, forces that constitute matter and radiation. The field also studies combinations of elementary particles up to the s ...
, it is used as a
scintillator A scintillator ( ) is a material that exhibits scintillation, the property of luminescence, when excited by ionizing radiation. Luminescent materials, when struck by an incoming particle, absorb its energy and scintillate (i.e. re-emit the ab ...
to detect high-energy
photon A photon () is an elementary particle that is a quantum of the electromagnetic field, including electromagnetic radiation such as light and radio waves, and the force carrier for the electromagnetic force. Photons are massless particles that can ...
s,
electron The electron (, or in nuclear reactions) is a subatomic particle with a negative one elementary charge, elementary electric charge. It is a fundamental particle that comprises the ordinary matter that makes up the universe, along with up qua ...
s, or
alpha particle Alpha particles, also called alpha rays or alpha radiation, consist of two protons and two neutrons bound together into a particle identical to a helium-4 nucleus. They are generally produced in the process of alpha decay but may also be produce ...
s. Plastics, such as polyvinyltoluene, can be doped with anthracene to produce an approximately water-equivalent scintillator in
radiation therapy Radiation therapy or radiotherapy (RT, RTx, or XRT) is a therapy, treatment using ionizing radiation, generally provided as part of treatment of cancer, cancer therapy to either kill or control the growth of malignancy, malignant cell (biology), ...
dosimetry Radiation dosimetry in the fields of health physics and radiation protection is the measurement, calculation and assessment of the ionizing radiation dose absorbed by an object, usually the human body. This applies both internally, due to ingest ...
. Anthracene is commonly used as a UV tracer in conformal coatings applied to printed wiring boards. The anthracene tracer allows the conformal coating to be inspected under UV light. It is also used in
wood Wood is a structural tissue/material found as xylem in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulosic fibers that are strong in tension and embedded in a matrix of lignin t ...
preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or ...
s,
insecticide Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...
s, and coating
materials A material is a substance or mixture of substances that constitutes an object. Materials can be pure or impure, living or non-living matter. Materials can be classified on the basis of their physical and chemical properties, or on their ge ...
.


Derivatives

A variety of anthracene derivatives find specialized uses. Industrially, anthracene is converted mainly to
anthraquinone Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic hydrocarbon, aromatic organic compound with formula . Several isomers exist but these terms usually refer to 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein th ...
, a precursor to dyes.Collin, Gerd; Höke, Hartmut and Talbiersky, Jörg (2006) "Anthracene" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim. Derivatives having a
hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to
phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...
and
naphthol Naphthol may refer to: * 1-Naphthol 1-Naphthol, or α-naphthol, is an organic compound with the formula . It is a fluorescent white solid. 1-Naphthol differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ...
s, and hydroxyanthracene (also called anthrol, and anthracenol) are
pharmacologically Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur between ...
active. Anthracene may also be found with multiple hydroxyl groups, as in
9,10-dihydroxyanthracene 9,10-Dihydroxyanthracene is an organic compound with the formula C14H10O2. It is the hydroquinone form of Anthraquinone, 9,10-anthraquinone (AQ). It formed when AQ is hydrogenated. It is easily dissolved in alkaline solutions and is often called ...
. Some anthracene derivatives are used as pharmaceutical drugs, including bisantrene, trazitiline, and benzoctamine.


Toxicology

Many investigations indicate that anthracene is noncarcinogenic: "consistently negative findings in numerous in vitro and in vivo genotoxicity tests". Early experiments suggested otherwise because crude samples were contaminated with other polycyclic aromatic hydrocarbons. Furthermore, it is readily biodegraded in soil. It is especially susceptible to degradation in the presence of light. The
International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; ) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and coordinate research into the causes of cancer. It also cance ...
(IARC) classifies anthracene as
IARC group 2B IARC group 2B substances, mixtures and exposure circumstances are those that have been classified as "possibly carcinogenic to humans" by the International Agency for Research on Cancer (IARC) as This category is used when there is level of evide ...
, possibly carcinogenic to humans.


See also

* 9,10-Dithioanthracene, derivative with two thiol groups added to the central ring *
Phenanthrene 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, expl ...
*
Acridine Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups ...
*
Phenazine Phenazine is an organic compound with the formula (C6H4)2N2. It is a dibenzo annulation, annulated pyrazine, and the parent substance of many dyestuffs, such as the toluylene red, indulines, and safranines (and the closely related eurhodines). Phe ...
* Tetracene


References


Cited sources

*


External links

*
IARC – Monograph 32


* ttps://web.archive.org/web/20110122105255/http://echa.europa.eu/home_en.asp European Chemicals Agency – ECHA* {{Authority control Organic semiconductors Phosphors and scintillators IARC Group 2B carcinogens Ionising radiation detectors Acenes PBT substances Polycyclic aromatic hydrocarbons