Terthiophene is the
organic compound with the formula
4H3Ssub>2C
4H
2S. It is an
oligomer
In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
of the heterocycle
thiophene, a shorter oligomer is dithienyl, and the parent polymer is
polythiophene. In the most common
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
of terthiophene, two thienyl groups are connected via their 2 positions to a central thiophene, also at the carbon atoms flanking the sulfur.
Preparation of terthiophene
Terthiophene is prepared by the nickel- or palladium-catalysed
coupling reaction of 2,5-dibromothiophene with the Grignard reagent derived from 2-bromothiophene.
Properties and applications
This isomer is a pigment in African
marigold
Marigold may refer to:
* Marigold (color), a yellow-orange color
It may also refer to:
Plants
* In the genus ''Calendula'':
** Common marigold, '' Calendula officinalis'' (also called pot marigold, ruddles, or Scotch marigold)
* In the genus ' ...
s (''
Tagetes'' spp.) and exhibits some biological activity because it sensitizes the formation of
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 ...
. It is responsible for the insecticidal activity of ''Tagetes minuta''.
Together with derivatives of
2,2'-bithiophene
2,2′-Bithiophene is the organic compound. It is a colorless solid, although commercial samples are often greenish. It is the most common of the three isomers with formula (C4H3S)2. The other two isomers have the connectivity 2,3′- and 3,3†...
, various substituted terthiophenes occur naturally. Examples include 5,5
''-dichloro-α-terthiophene, 5-chloro-α-terthiophene, 5-acetyl α-terthiophene, and 5-carboxyl bithiophene.
Terthiophene has been employed as building block for the organic semi-conductor polythiophene.
See also
*
Biphenyl
Biphenyl (also known as diphenyl, phenylbenzene, 1,1′-biphenyl, lemonene or BP) is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one ...
*
Terphenyl
*
Terpyridine
References
{{reflist
Thiophenes