241636
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:
Molecular Weight:
166.26
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
EC Number:
207-767-2
Beilstein/REAXYS Number:
3039
MDL number:
Product Name
2,2′-Bithiophene, 99%
InChI key
OHZAHWOAMVVGEL-UHFFFAOYSA-N
InChI
1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H
SMILES string
c1csc(c1)-c2cccs2
assay
99%
bp
260 °C (lit.)
mp
32-33 °C (lit.)
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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.
General description
2,2′-Bithiophene is an electron transporting material with the π-electrons present in the system that facilitate charge mobility.
Storage Class
10 - Combustible liquids
wgk
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)
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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.
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
Shuichi Yanagisawa et al.
Journal of the American Chemical Society, 128(36), 11748-11749 (2006-09-07)
A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO){P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes/arenes with aryl/heteroaryl iodides
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