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241636

Sigma-Aldrich

2,2′-Bithiophene

99%

Synonyme(s) :

2,2′-Bithienyl, 2,2′-Dithienyl

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About This Item

Formule empirique (notation de Hill):
C8H6S2
Numéro CAS:
492-97-7
Poids moléculaire :
166.26
Numéro Beilstein :
3039
Numéro CE :
207-767-2
Numéro MDL:
MFCD00005414
Code UNSPSC :
12352103
ID de substance PubChem :
24854316
Nomenclature NACRES :
NA.23

Pureté

99%

Point d'ébullition

260 °C (lit.)

Pf

32-33 °C (lit.)

Chaîne SMILES 

c1csc(c1)-c2cccs2

InChI

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

Clé InChI

OHZAHWOAMVVGEL-UHFFFAOYSA-N

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Description générale

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.

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

230.0 °F - closed cup

Point d'éclair (°C)

110 °C - closed cup

Équipement de protection individuelle

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

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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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