2,2'-bithiophene

CAS Number 492-97-7

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

High purity 2,2'-bithiophene, for applications in organic electronics

For the synthesis of small molecules or polymer semiconductors

Specifications | MSDS | Literature and Reviews

2,2'-bithiophene (CAS number 492-97-7) 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

A synthesis precusor

For bithiophene backboned polymers

Bithiophene building block

For semiconductors, OFETs, and solar cells

Worldwide shipping

Quick and reliable shipping

High purity

>99% High purity

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

Chemical Structure

Product Details

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

Characterisation 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 MSDS sheet

Literature and Reviews

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.
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.
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.

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).
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).
A Binaphthyl–Bithiophene Copolymer for Light Emitting Devices, Y. Li et al., Macromol. Chem. Phys., 203, 37–40 (2002).
A high-mobility electron-transporting polymer for printed transistors, H. Yan et al., nature, 457, 679 (2009).