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Sigma-Aldrich

2,2′-Bithiophene

99%

Synonym(s):

2,2′-Bithienyl, 2,2′-Dithienyl

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About This Item

Empirical Formula (Hill Notation):
C8H6S2
CAS Number:
492-97-7
Molecular Weight:
166.26
Beilstein/REAXYS Number:
3039
EC Number:
207-767-2
MDL number:
MFCD00005414
UNSPSC Code:
12352103
PubChem Substance ID:
24854316
NACRES:
NA.23

assay

99%

bp

260 °C (lit.)

mp

32-33 °C (lit.)

SMILES string

c1csc(c1)-c2cccs2

InChI

1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H

InChI key

OHZAHWOAMVVGEL-UHFFFAOYSA-N

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General description

2,2′-Bithiophene is an electron transporting material with the π-electrons present in the system that facilitate charge mobility.

Application

2,2′-Bithiophene can be polymerized to form poly(2,2′-Bithiophene) which can be electrodeposited on indium tin oxide (ITO) substrates for the fabrication of electrochromic devices. It can also be used in the formation of electrode material for the development of supercapacitors.
Substrate used in a rhodium-catalyzed C-H arylation of heteroarenes with aryl iodides.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

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Electrode material dependent p-or n-like thermoelectric behavior of single electrochemically synthesized poly (2, 2?-bithiophene) layer?application to thin film thermoelectric generator.
Kublitski J, et al.
Journal of Solid State Electrochemistry, 20(8), 2191-2196 (2016)
5, 5 `-Bis (dimesitylboryl)-2, 2 `-bithiophene and 5, 5 ``-bis (dimesitylboryl)-2, 2 `: 5 `, 2 ``-terthiophene as a novel family of electron-transporting amorphous molecular materials.
Noda T and Shirota Y
Journal of the American Chemical Society, 120(37), 9714-9715 (1998)
Weiying He et al.
Nature communications, 9(1), 3866-3866 (2018-09-27)
Nickel-catalyzed catalyst transfer polycondensation (CTP) of thiophenes is an efficient strategy for the controlled synthesis of polythiophenes. However, a detailed view of its reaction mechanism has remained elusive with unresolved questions regarding the geometry and bonding of critical Ni(0) thiophene intermediates.
Applications of Poly (indole-6-carboxylic acid-co-2, 2?-bithiophene) Films in High-Contrast Electrochromic Devices.
Kuo C, et al.
Coatings, 8(3), 102-102 (2018)
M Zangoli et al.
Nanoscale, 9(26), 9202-9209 (2017-06-27)
We report that nanoparticles prepared from appropriately functionalized polythiophenes once administered to live cells can acquire phototransduction properties under illumination, becoming photoactive sites able to absorb visible light and convert it to an electrical signal through cell membrane polarization. Amine-reactive
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