Names | |
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Preferred IUPAC name 12,22:25,32-Terthiophene | |
Other names α-Terthienyl 2,5-Di(2-thienyl)thiophene | |
Identifiers | |
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3D model (JSmol) | |
178604 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.168.218 |
EC Number |
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KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C12H8S3 | |
Molar mass | 248.39 g/mol |
Appearance | pale yellow solid |
Melting point | 93-95 °C |
insoluble | |
Hazards [1] | |
Main hazards | flammable |
GHS pictograms | |
GHS Signal word | Warning |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Related compounds | |
Related compounds | Thiophene polythiophene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
Infobox references | |
Terthiophene is the organic compound with the formula [C4H3S]2C4H2S. It is an oligomer of the heterocycle thiophene, a shorter oligomer is dithienyl, and the parent polymer is polythiophene. In the most common isomer of terthiophene, two thienyl groups are connected via their 2 positions to a central thiophene, also at the carbon atoms flanking the sulfur.
Terthiophene is prepared by the nickel- or palladium-catalysed coupling reaction of 2,5-dibromothiophene with the Grignard reagent derived from 2-bromothiophene. [2]
This isomer is a pigment in African marigolds ( Tagetes spp.) and exhibits some biological activity because it sensitizes the formation of singlet oxygen. [3] It is responsible for the insecticidal activity of Tagetes minuta. [4]
Together with derivatives of 2,2'-bithiophene, various substituted terthiophenes occur naturally. Examples include 5,5''-dichloro-α-terthiophene, 5-chloro-α-terthiophene, 5-acetyl α-terthiophene, and 5-carboxyl bithiophene. [5]
Terthiophene has been employed as building block for the organic semi-conductor polythiophene.
In chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Porphyrins are a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges (=CH−). The parent of porphyrin is porphine, a rare chemical compound of exclusively theoretical interest. Substituted porphines are called porphyrins. With a total of 26 π-electrons, of which 18 π-electrons form a planar, continuous cycle, the porphyrin ring structure is often described as aromatic. One result of the large conjugated system is that porphyrins typically absorb strongly in the visible region of the electromagnetic spectrum, i.e. they are deeply colored. The name "porphyrin" derives from the Greek word πορφύρα (porphyra), meaning purple.
Tagetes is a genus of annual or perennial, mostly herbaceous plants in the sunflower family Asteraceae. They are among several groups of plants known in English as marigolds. The genus Tagetes was described by Carl Linnaeus in 1753.
Viologens are organic compounds with the formula (C5H4NR)2n+. In some viologens, the pyridyl groups are further modified.
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.
Cinnamaldehyde is an organic compound with the formula C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde.
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula C
14H
8O
2. Isomers include various quinone derivatives. The term anthraquinone, however refers to the isomer, 9,10-anthraquinone wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.
Poly(p-phenylene vinylene) is a conducting polymer of the rigid-rod polymer family. PPV is the only polymer of this type that can be processed into a highly ordered crystalline thin film. PPV and its derivatives are electrically conducting upon doping. Although insoluble in water, its precursors can be manipulated in aqueous solution. The small optical band gap and its bright yellow fluorescence makes PPV a candidate in applications such as light-emitting diodes (LED) and photovoltaic devices. Moreover, PPV can be doped to form electrically conductive materials. Its physical and electronic properties can be altered by the inclusion of functional side groups.
Polythiophenes (PTs) are polymerized thiophenes, a sulfur heterocycle. The parent PT is an insoluble colored solid with the formula (C4H2S)n. The rings are linked through the 2- and 5-positions. Poly(alkylthiophene)s have alkyl substituents at the 3- or 4-position(s). They are also colored solids, but tend to be soluble in organic solvents.
In chemistry, diarylethene is the general name of a class of compounds that have aromatic groups bonded to each end of a carbon–carbon double bond. The simplest example is stilbene, which has two geometric isomers, E and Z.
Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur is essential for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.
Benzothiophene is an aromatic organic compound with a molecular formula C8H6S and an odor similar to naphthalene (mothballs). It occurs naturally as a constituent of petroleum-related deposits such as lignite tar. Benzothiophene has no household use. In addition to benzo[b]thiophene, a second isomer is known: benzo[c]thiophene.
Benzoxazole is an aromatic organic compound with a molecular formula C7H5NO, a benzene-fused oxazole ring structure, and an odor similar to pyridine. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important.
Phototoxins are toxins that can cause allergic reactions in particularly susceptible individuals and which can cause dangerous photosensitivity in a much broader range of subjects.
α-Eleostearic acid or (9Z,11E,13E)-octadeca-9,11,13-trienoic acid, is an organic compound, a conjugated fatty acid and one of the isomers of octadecatrienoic acid. It is often called simply eleostearic acid although there is also a β-eleostearic acid. Its high degree of unsaturation gives tung oil its properties as a drying oil.
1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.
Xylylene (sometimes quinone-dimethides) comprises two isomeric organic compounds with the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene are best known, although neither is stable in solid or liquid form. The meta form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, an example being tetracyanoquinodimethane.
Thienothiophene usually refers to any of three structurally related derivatives of thiophene with the formula C6H4S2. In order of importance, they are: thieno(3,2-b)thiophene, thieno(2,3-b)thiophene, and thieno(3,4-b)thiophene. Other isomers feature S(IV) and are less stable. Thieno[2,3-b]thiophene was the first member of the series to be isolated. It was obtained in very low yield upon heating citric acid, a source of a six-carbon linear chain, with P4S10. More efficient syntheses of this and the other two stable thienothiophenes involve cyclization reactions of substituted thiophenes.
1,2-Dioxolane is a chemical compound with formula C3H6O2, consisting of a ring of three carbon atoms and two oxygen atoms in adjacent positions. Its structural formula could be written as [–(CH
2)3–O–O–].