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| Identifiers | |
|---|---|
3D model (JSmol) | |
| 1915988 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.005.349 |
| EC Number |
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PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C30H16 | |
| Molar mass | 376.458 g/mol |
| Appearance | reddish-brown or yellowish |
| Density | 1.4±0.1 g/cm3 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Pyranthrene is a molecule with the chemical formula C30H16. [1]
Pyranthrene is made up of eight benzene rings fused together, which classes it as a polycyclic aromatic hydrocarbon. [1]
It has a reddish-brown color, but turns to a yellowish color when it is purified via sublimation. The difference between these two forms of the molecule comes from the difference in the degrees of their crystallinity. The brown form of pyranthrene forms more perfect crystallites than the yellow form does. [2]
Pyranthrene is also an organic semiconductor. It displays photoconductive properties when it is in a solid state, [3] as well as when it is dissolved in a benzene solution. [4]
It has a density of 1.4±0.1 g/cm3. [5]
Pyranthrene has potential uses as a material used to make organic light-emitting diodes and solar cells. [6] [3]
In addition, it has photophysical properties that allow it to be useful for biological imaging and sensing. However, pyranthrene has been shown to cause oxidative stress and DNA damage within cells, [6] and is classed as a carcinogen and an endocrine disruptor, which heavily limits its use in biological systems. [7]
Pyranthrene can be synthesized by reducing pyranthrone with zinc dust, acetic acid, and pyridine. [8]
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected by the stabilization of conjugation alone. The earliest use of the term was in an article by August Wilhelm Hofmann in 1855. There is no general relationship between aromaticity as a chemical property and the olfactory properties of such compounds.
In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures into a resonance hybrid in valence bond theory. It has particular value for analyzing delocalized electrons where the bonding cannot be expressed by one single Lewis structure. The resonance hybrid is the accurate structure for a molecule or ion; it is an average of the theoretical contributing structures.
Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O), selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.
In organic chemistry, Hückel's rule predicts that a planar ring molecule will have aromatic properties if it has 4n + 2 π-electrons, where n is a non-negative integer. The quantum mechanical basis for its formulation was first worked out by physical chemist Erich Hückel in 1931. The succinct expression as the 4n + 2 rule has been attributed to W. v. E. Doering (1951), although several authors were using this form at around the same time.
An alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applicable to organic synthesis. Being a cycloaddition reaction, it has high atom economy. Many variations have been developed, including cyclisation of mixtures of alkynes and alkenes as well as alkynes and nitriles.
In organic chemistry, helicenes are ortho-condensed polycyclic aromatic compounds in which benzene rings or other aromatics are angularly annulated to give helically-shaped chiral molecules. The chemistry of helicenes has attracted continuing attention because of their unique structural, spectral, and optical features.
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.
Cycloheptatriene (CHT) is an organic compound with the formula C7H8. It is a closed ring of seven carbon atoms joined by three double bonds (as the name implies) and four single bonds. This colourless liquid has been of recurring theoretical interest in organic chemistry. It is a ligand in organometallic chemistry and a building block in organic synthesis. Cycloheptatriene is not aromatic, as reflected by the nonplanarity of the methylene bridge (-CH2-) with respect to the other atoms; however the related tropylium cation is.
The Zincke–Suhl reaction is a special case of a Friedel-Crafts alkylation and was first described by Theodor Zincke and Suhl in 1906. Unlike the traditional Friedel-Crafts reaction, the reduction of the phenyl ring leads to a higher energy final product that can be used as starting material in the dienol–benzene rearrangement, among other reactions.
In organic and physical organic chemistry, Clar's rule is an empirical rule that relates the chemical stability of a molecule with its aromaticity. It was introduced in 1972 by the Austrian organic chemist Erich Clar in his book The Aromatic Sextet. The rule states that given a polycyclic aromatic hydrocarbon, the resonance structure most important to characterize its properties is that with the largest number of aromatic π-sextets i.e. benzene-like moieties.
β-Alanine ethyl ester is the ethyl ester of the non-essential amino acid β-alanine. It would be expected to hydrolyse within the body to form β-alanine.
Hexamethylbenzene, also known as mellitene, is a hydrocarbon with the molecular formula C12H18 and the condensed structural formula C6(CH3)6. It is an aromatic compound and a derivative of benzene, where benzene's six hydrogen atoms have each been replaced by a methyl group. In 1929, Kathleen Lonsdale reported the crystal structure of hexamethylbenzene, demonstrating that the central ring is hexagonal and flat and thereby ending an ongoing debate about the physical parameters of the benzene system. This was a historically significant result, both for the field of X-ray crystallography and for understanding aromaticity.
Chavibetol is an organic chemical compound of the phenylpropanoid class. It is one of the primary constituents of the essential oil from the leaves of the betel plant and catatia. It is an aromatic compound with a spicy odor.
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.
Urushibara nickel is a nickel-based hydrogenation catalyst. It is a heterogeneous catalyst, comparable to Raney nickel. Urushibara nickel is however not pyrophoric. For most hydrogenations, it performs comparably to W-7 grade Raney nickel.
Hexa-peri-hexabenzocoronene (HBC) is a polycyclic aromatic hydrocarbon with the molecular formula C42H18. It consists of a central coronene molecule, with an additional benzene ring fused between each adjacent pair of rings around the periphery. It is sometimes simply called hexabenzocoronene, however, there are other chemicals that share this less-specific name, such as hexa-cata-hexabenzocoronene.
Violanthrone, also known as dibenzanthrone, is an organic compound that serves as a vat dye and a precursor to other vat dyes. X-ray crystallography confirms that the molecule is planar with C2v symmetry. Isomeric with violanthrone is isoviolanthrone, which has a centrosymmetric structure.
Rhodium-platinum oxide , or Nishimura's catalyst, is an inorganic compound used as a hydrogenation catalyst.
In organic chemistry, the Murai reaction is an organic reaction that uses C-H activation to create a new C-C bond between a terminal or strained internal alkene and an aromatic compound using a ruthenium catalyst. The reaction, named after Shinji Murai, was first reported in 1993. While not the first example of C-H activation, the Murai reaction is notable for its high efficiency and scope. Previous examples of such hydroarylations required more forcing conditions and narrow scope.
Teruaki Mukaiyama was a Japanese organic chemist. One of the most prolific chemists of the 20th century in the field of organic synthesis, Mukaiyama helped establish the field of organic chemistry in Japan after World War II.
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