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2,2'-bithiophene

2,2'-bithiophene chemical structure
Product Code B321
Price $64.00 ex. VAT
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2,2'-bithiophene is an intermediate widely used for the synthesis of small molecules or polymer semiconductors in application of organic electronics. It has proven that 2,2'-bithiophene exists as a mixture of the cis-like and the trans-like planar structures. 5,5'-positions of 2,2'-bithiophene are easily accessible for bromination and stannylation to give 5,5'-dibromo-2,2'-bithiophene or 5,5'-trimethylstannyl-2,2'-bithiophene, which can be used for direct arylation reactions.

Synthesis of 5,5-dibromo-2,2-bithiophene
Synthesis of 5,5’-dibromo-2,2’-bithiophene from 2,2’-bithiophene reacting with NBS in CHCl3

General Information

CAS number 492-97-7
Chemical formula C8H6S2
Molecular weight 166.26 g/mol
Synonyms

2,2′-Bithienyl, 2,2′-Dithienyl
2-(2-thienyl)thiophene
2-(thien-2-yl)thiophene
Classification / Family

Thiophene, Bithiophene, Heterocyclic five-membered ring, Organic materials, Semiconductor Synthesis, Low band gap polymers, OFETs, Organic Photovoltaics, Polymer Solar Cells

Product Details

Purity  99%
Melting point 32-33 °C
Appearance Yellowish liquid/solid

Chemical Structure

Chemical structure of 2,2-bithiophene. CAS number 492-97-7. Chemical formula C8H6S2.

Charaterisation by 1H-NMR (example)

1H NMR bithiophene in CDCl3
1H NMR spectrum of 2,2’-bithiophene in CDCl3: Instrument AVIIIHD400 (view full version)

MSDS Documentation

2,2'-bithiophene MSDS2,2'-bithiophene MSDS sheet

Literature and Reviews

  1. White light from an electroluminescent diode made from poly[3(4‐octylphenyl)‐2,2’‐bithiophene] and an oxadiazole derivative, M. Berggren et al, J. Appl. Phys. 76, 7530 (1994); http://dx.doi.org/10.1063/1.357984.
  2. Electronic structure of thiophene and pyrrole dimers: 2,2’‐bithiophene, 2,2’‐thienylpyrrole, and 2,2’‐bipyrrole, D. Birnbaum et al., J. Chem. Phys. 95, 4783 (1991); http://dx.doi.org/10.1063/1.461721.
  3. Highly Efficient Light-Harvesting Ruthenium Sensitizer for Thin-Film Dye-Sensitized Solar Cells, C-Y. Chen et al., ACS Nano, 3 (10), 3103–3109 (2009); DOI: 10.1021/nn900756s.
  4. 3,6-Di(furan-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione and bithiophene copolymer with rather disordered chain orientation showing high mobility in organic thin film transistors, Y. Li et al., J. Mater. Chem., 21, 10829-10835 (2011).
  5. Indolo[3,2-b]carbazole-based alternating donor–acceptor copolymers: synthesis, properties and photovoltaic application, E. Zhou et al., J. Mater. Chem., 19, 7730-7737 (2009).
  6. A Binaphthyl–Bithiophene Copolymer for LightEmitting Devices, Y. Li et al., Macromol. Chem. Phys., 203, 37–40 (2002).
  7. A high-mobility electron-transporting polymer for printed transistors, H. Yan et al., nature, 457, 679 (2009).

To the best of our knowledge the information provided here is accurate. However, Ossila assume no liability for the accuracy of this page. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. All products are for laboratory and research and development use only, and may not be used for any other purpose including health care, pharmaceuticals, cosmetics, food or commercial applications.

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