![Fluorescence of Anthracene under UV light](https://upload.wikimedia.org/wikipedia/commons/4/42/Fluorescence_of_Anthracene_under_UV_light.jpg)
Anthracene is a solid
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. ...
(PAH) of formula C
14H
10, consisting of three fused
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
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 psoriasi ...
. 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 stati ...
of the red
dye
A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution an ...
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 prominent red dye, principally for dyeing textile fabrics. Histori ...
and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak)
fluorescence
Fluorescence is the emission of light by a substance that has absorbed light or other electromagnetic radiation. It is a form of luminescence. In most cases, the emitted light has a longer wavelength, and therefore a lower photon energy, tha ...
under
ultraviolet
Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than ...
radiation.
Occurrence and production
Coal tar, which contains around 1.5% anthracene, remains a major 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 and pesticides, e ...
and
carbazole
Carbazole is an aromatic 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 based on the indole str ...
. 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 The Elbs reaction is an organic reaction describing the pyrolysis of an ortho methyl substituted benzophenone to a condensed polyaromatic. The reaction is named after its inventor, the German chemist Karl Elbs, also responsible for the Elbs oxid ...
, 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
9,10-Dihydroanthracene is an organic compound that is derived from the polycyclic aromatic hydrocarbon anthracene. Several isomers of dihydroanthracene are known, but the 9,10 derivative is most common. It is a colourless solid that is used as a ...
, preserving the aromaticity of the two flanking rings.
Cycloadditions
Anthracene
photodimerizes by the action of
UV light:
:
The
dimer
Dimer may refer to:
* Dimer (chemistry), a chemical structure formed from two similar sub-units
** Protein dimer, a protein quaternary structure
** d-dimer
* Dimer model, an item in statistical mechanics, based on ''domino tiling''
* Julius Dimer ...
, called dianthracene (or sometimes paranthracene), is connected by a pair of new carbon-carbon bonds, the result of the
+4cycloaddition
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 the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...
.
Anthracene also reacts with dienophile
singlet oxygen
Singlet oxygen, systematically named dioxygen(singlet) and dioxidene, is a gaseous inorganic chemical with the formula O=O (also written as or ), which is in a quantum state where all electrons are spin paired. It is kinetically unstable at ambie ...
in a
+2cycloaddition (
Diels–Alder reaction
In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a peric ...
):
:
With electrophiles
Chemical
oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
occurs readily, giving
anthraquinone
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxo ...
, C
14H
8O
2 (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 viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%†...
and
vanadyl acetylacetonate
Vanadyl acetylacetonate is the chemical compound with the 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 coordination complex consists of the vanadyl g ...
.
:
Electrophilic substitution of anthracene occurs at the 9 position. For example, formylation affords
9-anthracenecarboxaldehyde
Anthracene-9-carbaldehyde is the most common monoaldehyde derivative of anthracene. It is a yellow solid that is soluble in common organic solvents. It is prepared by Vilsmeier formylation of anthracene. The compound is also used as a building b ...
. Substitution at other positions is effected indirectly, for example starting with anthroquinone. Bromination of anthracene gives 9,10-dibromoanthracene.
Uses
Anthracene is converted mainly to
anthraquinone
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxo ...
, a precursor to dyes.
[Collin, Gerd; Höke, Hartmut and Talbiersky, Jörg (2006) "Anthracene" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim. ]
Niche
Anthracene, 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 or ...
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 absorbed ...
for detectors of 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, so they always ...
s,
electron
The electron ( or ) is a subatomic particle with a negative one elementary electric charge. Electrons belong to the first generation of the lepton particle family,
and are generally thought to be elementary particles because they have no kn ...
s and
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 a plastic
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 absorbed ...
that is approximately water-equivalent for use in
radiation therapy
Radiation therapy or radiotherapy, often abbreviated RT, RTx, or XRT, is a therapy using ionizing radiation, generally provided as part of cancer treatment to control or kill malignant cells and normally delivered by a linear accelerator. Radia ...
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 ingested o ...
. Anthracene's
emission spectrum
The emission spectrum of a chemical element or chemical compound is the spectrum of frequencies of electromagnetic radiation emitted due to an electron making a atomic electron transition, transition from a high energy state to a lower energy st ...
peaks at between 400 nm and 440 nm.
It is also used in
wood
Wood is a porous and fibrous structural tissue found in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulose fibers that are strong in tension and embedded in a matrix of lignin th ...
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 by ...
s,
insecticide
Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...
s, and coating
materials
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 geologic ...
.
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.
Derivatives
![Antracene diradical AFM2](https://upload.wikimedia.org/wikipedia/commons/3/35/Antracene_diradical_AFM2.png)
A variety of anthracene derivatives find specialized uses. 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 g ...
are 1-hydroxyanthracene and 2-hydroxyanthracene, homologous to
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...
and
naphthol Naphthol may refer to:
* 1-Naphthol
1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula . It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. ...
s, and hydroxyanthracene (also called anthrol, and anthracenol) are
pharmacologically 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 (C6H4CHOH)2. It is the hydroquinone form of 9,10-anthraquinone (AQ). It formed when AQ is hydrogenated. It is easily dissolved in alkaline solutions and is often called ''soluble ...
.
Occurrence
Anthracene, as many other
polycyclic aromatic hydrocarbons
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. P ...
, is generated during combustion processes. Exposure to humans happens mainly through tobacco smoke and ingestion of food contaminated with combustion products.
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.
[
]
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 and pesticides, e ...
* Tetracene
References
Cited sources
*
External links
Image
of anthracene crystals
*
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 3 carcinogens
Anthracenes
Ionising radiation detectors
Acenes
PBT substances
Polycyclic aromatic hydrocarbons