Perylene

Last updated
Perylene [1]
Perylene.svg
Perylene-3D-balls.png
Perylene sample.jpg
Names
Preferred IUPAC name
Perylene [2]
Other names
peri-Dinaphthalene; Perilene; Dibenz[de,kl]anthracene
Identifiers
  • 198-55-0 Yes check.svgY
3D model (JSmol)
1911335
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.365 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-900-9
104944
KEGG
PubChem CID
RTECS number
  • SE3794000
UNII
  • InChI=1S/C20H12/c1-5-13-6-2-11-17-18-12-4-8-14-7-3-10-16(20(14)18)15(9-1)19(13)17/h1-12H X mark.svgN
    Key: CSHWQDPOILHKBI-UHFFFAOYSA-N X mark.svgN
  • c1ccc5cccc4c5c1c2cccc3cccc4c23
Properties
C20H12
Molar mass 252.316 g·mol−1
AppearanceBrown solid
Melting point 276 to 279 °C (529 to 534 °F; 549 to 552 K)
-166.8·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry, perylene is used as a fluorescent lipid probe. It is the parent compound of a class of rylene dyes.

Contents

Reactions

Like other polycyclic aromatic compounds, perylene is reduced by alkali metals to give a deeply colored radical anion and a dianion. The diglyme solvates of these salts have been characterized by X-ray crystallography. [3]

Emission

Perylene displays blue fluorescence. It is used as a blue-emitting dopant material in OLEDs, either pure or substituted. Perylene can be also used as an organic photoconductor. It has an absorption maximum at 434 nm, and as with all polycyclic aromatic compounds, low water solubility (1.2 x 10−5 mmol/L). Perylene has a molar absorptivity of 38,500 M−1cm−1 at 435.7 nm.

Structure

Vat Red 29 typical example of a structure with a perylene core Vat Red 29.png
Vat Red 29 typical example of a structure with a perylene core

The perylene molecule consists of two naphthalene molecules connected by a carbon-carbon bond at the 1 and 8 positions on both molecules. All of the carbon atoms in perylene are sp2 hybridized. The structure of perylene has been extensively studied by X-ray crystallography. [4]

Biology

Naturally occurring perylene quinones have been identified in lichens Laurera sanguinaria Malme and Graphis haematites Fée. [5]

Related Research Articles

Organic chemistry Subdiscipline of chemistry

Organic chemistry is a branch of chemistry that studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical study.

Anthracene Chemical compound

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.

Coronene Chemical compound

Coronene is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings. Its chemical formula is C
24H
12. It is a yellow material that dissolves in common solvents including benzene, toluene, and dichloromethane. Its solutions emit blue light fluorescence under UV light. It has been used as a solvent probe, similar to pyrene.

Polycyclic aromatic hydrocarbon Hydrocarbon composed of multiple aromatic rings

A polycyclic aromatic hydrocarbon (PAH) is a hydrocarbon—a chemical compound containing only carbon and hydrogen—that is composed of multiple aromatic rings. The group is a major subset of the aromatic hydrocarbons. The simplest of such chemicals are naphthalene, having two aromatic rings, and the three-ring compounds anthracene and phenanthrene. The terms polyaromatic hydrocarbon or polynuclear aromatic hydrocarbon are also used for this concept.

Pyrene Chemical compound

Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is C16H10. This yellow solid is the smallest peri-fused PAH. Pyrene forms during incomplete combustion of organic compounds.

Radical anion free radical species

In organic chemistry, radical anion is a subset of charged free radical species that carry a negative charge. Radical anions are encountered in organic chemistry as reduced derivatives of polycyclic aromatic compounds, e.g. sodium naphthenide. An example of a non-carbon radical anion is the superoxide anion, formed by transfer of one electron to an oxygen molecule. Radical anions are typically indicated by .

A superbase is a compound that has a particularly high affinity for protons. Superbases are of theoretical interest and potentially valuable in organic synthesis. Superbases have been described and used since the 1850s.

Molecular electronic transitions take place when electrons in a molecule are excited from one energy level to a higher energy level. The energy change associated with this transition provides information on the structure of a molecule and determines many molecular properties such as colour. The relationship between the energy involved in the electronic transition and the frequency of radiation is given by Planck's relation.

Photochromism reversible chemical transformation by absorption of electromagnetic radiation

Photochromism is the reversible transformation of a chemical species (photoswitch) between two forms by the absorption of electromagnetic radiation (photoisomerization), where the two forms have different absorption spectra. In plain language, this can be described as a reversible change of colour upon exposure to light.

Metal aromaticity is the concept of aromaticity, found in many organic compounds, extended to metals. The first experimental evidence for the existence of aromaticity in metals was found in aluminium cluster compounds of the type MAl−
4 where M stands for lithium, sodium or copper. These anions can be generated in a helium gas by laser vaporization of an aluminium / lithium carbonate composite or a copper or sodium / aluminium alloy, separated and selected by mass spectrometry and analyzed by photoelectron spectroscopy. The evidence for aromaticity in these compounds is based on several considerations. Computational chemistry shows that these aluminium clusters consist of a tetranuclear Al2−
4 plane and a counterion at the apex of a square pyramid. The Al2−
4 unit is perfectly planar and is not perturbed the presence of the counterion or even the presence of two counterions in the neutral compound M
2Al
4. In addition its HOMO is calculated to be a doubly occupied delocalized pi system making it obey Hückel's rule. Finally a match exists between the calculated values and the experimental photoelectron values for the energy required to remove the first 4 valence electrons. The first fully metal aromatic compound was a cyclogallane with a Ga32- core discovered by Gregory Robinson in 1995.

Photodegradation

Photodegradation is the alteration of materials by light. Commonly, the term is used loosely to refer to the combined action of sunlight and air, which cause oxidation and hydrolysis. Often photodegradation is intentionally avoided, since it destroys paintings and other artifacts. It is, however, partly responsible for remineralization of biomass and is used intentionally in some disinfection technologies. Photodegradation does not apply to how materials may be aged or degraded via infrared light or heat, but does include degradation in all of the ultraviolet light wavebands.

Homoaromaticity Special case of aromaticity in which conjugation is interrupted by a single sp³ hybridized carbon atom

Homoaromaticity, in organic chemistry, refers to a special case of aromaticity in which conjugation is interrupted by a single sp3 hybridized carbon atom. Although this sp3 center disrupts the continuous overlap of p-orbitals, traditionally thought to be a requirement for aromaticity, considerable thermodynamic stability and many of the spectroscopic, magnetic, and chemical properties associated with aromatic compounds are still observed for such compounds. This formal discontinuity is apparently bridged by p-orbital overlap, maintaining a contiguous cycle of π electrons that is responsible for this preserved chemical stability.

Ovalene Chemical compound

Ovalene is a polycyclic aromatic hydrocarbon with the formula C32H14, which consists of ten peri-fused six-membered rings. It is very similar to coronene.

Desorption atmospheric pressure photoionization

Desorption atmospheric pressure photoionization (DAPPI) is an ambient ionization technique for mass spectrometry that uses hot solvent vapor for desorption in conjunction with photoionization. Ambient Ionization techniques allow for direct analysis of samples without pretreatment. The direct analysis technique, such as DAPPI, eliminates the extraction steps seen in most nontraditional samples. DAPPI can be used to analyze bulkier samples, such as, tablets, powders, resins, plants, and tissues. The first step of this technique utilizes a jet of hot solvent vapor. The hot jet thermally desorbs the sample from a surface. The vaporized sample is then ionized by the vacuum ultraviolet light and consequently sampled into a mass spectrometer. DAPPI can detect a range of both polar and non-polar compounds, but is most sensitive when analyzing neutral or non-polar compounds. This technique also offers a selective and soft ionization for highly conjugated compounds.

Croconic acid Chemical compound

Croconic acid or 4,5-dihydroxycyclopentenetrione is a chemical compound with formula C5H2O5 or (C=O)3(COH)2. It has a cyclopentene backbone with two hydroxyl groups adjacent to the double bond and three ketone groups on the remaining carbon atoms. It is sensitive to light, soluble in water and ethanol and forms yellow crystals that decompose at 212 °C.

Atmospheric pressure laser ionization is an atmospheric pressure ionization method for mass spectrometry (MS). Laser light in the UV range is used to ionize molecules in a resonance-enhanced multiphoton ionization (REMPI) process. It is a selective and sensitive ionization method for aromatic and polyaromatic compounds. Atmospheric photoionization is the latest in development of atmospheric ionization methods.

Olympicene Chemical compound

Olympicene is an organic carbon based molecule formed of five rings, of which four are benzene rings, joined in the shape of the Olympic rings.

A spiropyran is a type of organic chemical compound, known for photochromic properties that provide this molecule with the ability of being used in medical and technological areas. Spiropyrans were discovered in the early twentieth century. However, it was in the middle twenties when Fisher and Hirshbergin observed their photochromic characteristics and reversible reaction. In 1952, Fisher and co-workers announced for the first time photochromism in spiropyrans. Since then, there have been many studies on photochromic compounds that have continued up to the present.

Perylenetetracarboxylic dianhydride Chemical compound

Perylenetetracarboxylic dianhydride (PTCDA) is an organic dye molecule and an organic semiconductor. It is used as a precursor to a class of molecules known as Rylene dyes, which are useful as pigments and dyes. It is a dark red solid with low solubility in aromatic solvents. The compound has attracted much interest as an organic semiconductor.

Lithium naphthalene Chemical compound

Lithium naphthalene is an organic salt with the chemical formula Li+C
10H−
8. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It is usually generated in situ. Lithium naphthalene crystallizes with ligands bound to Li+.

References

  1. ↑ Perylene at Sigma-Aldrich
  2. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 206. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  3. ↑ Näther, Christian; Bock, Hans; Havlas, Zdenek; Hauck, Tim (1998). "Solvent-Shared and Solvent-Separated Ion Multiples of Perylene Radical Anions and Dianions: An Exemplary Case of Alkali Metal Cation Solvation". Organometallics. 17 (21): 4707–4715. doi:10.1021/om970610g.
  4. ↑ Donaldson, D. M.; Robertson, J. M.; White, J. G. (1953). "The crystal and molecular structure of perylene". Proceedings of the Royal Society A . 220 (1142): 311–321. Bibcode:1953RSPSA.220..311D. doi:10.1098/rspa.1953.0189. JSTOR   99329. S2CID   97262226.
  5. ↑ Annick Mathey, Wim Van Roy, Luc Van Vaeck, Gert Eckhardt, Wolfgang Steglich (1994). "In situ analysis of a new perylene quinone in lichens by Fourier-transform laser microprobe mass spectrometry with external source". Rapid Communications in Mass Spectrometry. 8 (1): 46–52. Bibcode:1994RCMS....8...46M. doi:10.1002/rcm.1290080109.CS1 maint: multiple names: authors list (link)
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