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311073

2,2′:5′,2′′-Terthiophene

Name: 2,2′:5′,2′′-Terthiophene
Brand: ALDRICH

99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₈S₃

CAS Number:

1081-34-1

Molecular Weight:

248.39

UNSPSC Code:

12352103

NACRES:

NA.23

PubChem Substance ID:

24858835

MDL number:

MFCD00012167

Beilstein/REAXYS Number:

178604

Assay:

99%

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Properties

Quality Level

200

assay

99%

mp

93-95 °C (lit.)

SMILES string

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

InChI key

KXSFECAJUBPPFE-UHFFFAOYSA-N

Description

General description

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Excess-electron injection and transfer in terthiophene-modified DNA: terthiophene as a photosensitizing electron donor for thymine, cytosine, and adenine.

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)

Electropolymerized molecularly imprinted polymer films of a bis-terthiophene dendron: folic acid quartz crystal microbalance sensing.

Dahlia C Apodaca et al.

ACS applied materials & interfaces, 3(2), 191-203 (2010-11-18)

A folic acid sensor was prepared via an electropolymerized molecularly imprinted polymer (E-MIP) film of a bis-terthiophene dendron on a quartz crystal microbalance (QCM). The cyclic voltammetry (CV) electrodeposition of the imprinted polymer film was monitored by electrochemical QCM or

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Global Trade Item Number

SKU	GTIN
311073-1G	04061826678015