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Sigma-Aldrich

2,2′:5′,2′′-Terthiophene

99%

Synonyme(s) :

α-Terthienyl, 2,5-Di(2-thienyl)thiophene

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About This Item

Formule empirique (notation de Hill):
C12H8S3
Numéro CAS:
1081-34-1
Poids moléculaire :
248.39
Numéro Beilstein :
178604
Numéro MDL:
MFCD00012167
Code UNSPSC :
12352103
ID de substance PubChem :
24858835
Nomenclature NACRES :
NA.23

Pureté

99%

Pf

93-95 °C (lit.)

Chaîne SMILES 

c1csc(c1)-c2ccc(s2)-c3cccs3

InChI

1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H

Clé InChI

KXSFECAJUBPPFE-UHFFFAOYSA-N

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Description générale

2,2′:5′,2′′-Terthiophene (3T) is a tri-thiophene based low band conductive polymer that is prepared by reacting 2,5-dibromothiophene and thienylmagnesium bromide in the presence of nickel catalyst.
2,2′:5′,2′′-Terthiophene (TTh) may be prepared by nickel catalysed coupling reaction of grignard′s reagent derived from 2-bromothiophene and magnesium. It generates singlet oxygen. In nature, it is found in the floral extract of Tagetes minuta and Echinops grijisii. It is known to be toxic to mosquitoes. It also exihibits antifungal activity.

Application

3T can be combined with 3,4-ethylenedioxythiophene (EDOT) in a tetrabutylammonium perchlorate solution for use as an electrochromic copolymer for a wide range of applications like photovoltaics and polymer light emitting diodes (LEDs). It can also be used to form metal-organic based thin films with metals like aluminum, silver, and calcium which can potentially be used for optoelectronics based applications.
Electrochemical copolymerization of carbazole and TTh in sodium perchlorate/acetonitrile was reported. Electrochromic copolymer based on TTh and 3, 4-ethylenedioxythiophene has been reported. TTh acts as a monomer precursor for polythiophene and as a dopant for polycarbonate. It may function as a photosensitizer.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Sanami Yazaki et al.
Journal of the American Chemical Society, 132(22), 7702-7708 (2010-05-15)
New molecular materials combining ionic and electronic functions have been prepared by using liquid crystals consisting of terthiophene-based mesogens and terminal imidazolium groups. These liquid crystals show thermotropic smectic A phases. Nanosegregation of the pi-conjugated mesogens and the ionic imidazolium
M J Perich et al.
Journal of the American Mosquito Control Association, 11(3), 307-310 (1995-09-01)
Application of Tagetes minuta floral extract to silica gel column chromatography produced 2 fractions with the hydrogenate part 20-30 times more toxic to larvae and 12-13 times more toxic to adults of Aedes aegypti and Anopheles stephensi, respectively, than the
Generation of singlet oxygen by 2,2:5,2-terthiophene and some of its derivatives.
Ciofalo M, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 83(1), 1-6 (1194)
Bulletin of the Chemical Society of Japan, 66, 2960-2960 (1993)
Man Jae Park et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(7), 2056-2062 (2012-01-18)
Excess-electron transfer (EET) in DNA has attracted wide attention owing to its close relation to DNA repair and nanowires. To clarify the dynamics of EET in DNA, a photosensitizing electron donor that can donate an excess electron to a variety
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