2,2'-bithiophene

Order Code: B321
MSDS sheet

Price

(excluding Taxes)

£49.00


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
Color Yellowish liquid/solid

 

 

Chemical Structure

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

Applications

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

NMR Charaterisation

 

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

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).