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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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Catégories apparentées

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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Synthesis and characterization of an electrochromic copolymer based on 2, 2′ : 5′ , 2″ -terthiophene and 3, 4-ethylenedioxythiophene
Ahmed MS, et al.
Applied Nanoscience, 2(2), 133-141 (2012)
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
Journal of Non-Crystalline Solids, 164, 1263-1263 (1993)
Hui-Bog Noh et al.
Biomaterials, 33(9), 2600-2607 (2012-01-03)
A highly sensitive in vivo biosensor for glutathione disulfide (GSSG) is developed using covalently immobilized-glutathione reductase (GR) and -β-nicotinamide adenine dinucleotide phosphate (NADPH) on gold nanoparticles deposited on poly[2,2':5',2″-terthiophene-3'-(p-benzoic acid)] (polyTTBA). The fabricated biosensor was characterized with SEM, TEM, XPS
Synthesis and characterization of an electrochromic copolymer based on 2,2':5',"-terthiophene and 3,4-ethylenedioxythiophene
Ahmed MS, et al.
Applied Nanoscience, 2, 133-141 (2012)
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