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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:
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.

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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.
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)
Ji He et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 16(7), 1049-1056 (2017-05-13)
Three D-D-π-A triphenylamine-coumarin sensitizers were designed and synthesized with a triphenylamine and coumarin double donor and a cyanoacrylic acid acceptor. Thiophene, bithiophene and phenylthiophene were used as π-bridges, respectively, and the effects of different π-bridges on the photophysical properties and
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)
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