Thieno[3,2-b]thiophene-2-carbonitrile


Order Code: B281
Not in stock

General Information

CAS number 40985-58-8
Chemical formula C7H3NS2
Molecular weight 165.23 g/mol
Synonyms  2-Cyanothieno[3,2-b]thiophene 
Classification / Family Thiophene, Thienothiophene, Fused thiophene, Heterocyclic five-membered ring, Organic materials, Semiconductor synthesis, Low band gap polymers, OFETs, Organic photovoltaics, Polymer solar cells

Product Details

Purity  98%
Melting point  48-50 °C
Color Off-white powder/crystals

 

chemical structure thienothiophene-2-carbonitrile
Chemical structure of Thieno[3,2-b]thiophene-2-carbonitrile. CAS number: 40985-58-8. Chemical formula: C7H3NS2.

 

Applications

Thieno[3,2-b]thiophene-2-carbonitrile, also known as 2-Cyanothieno[3,2-b]thiophene, belongs to the family of fused thiopehenes which are electron-rich and structurally rigid with extended π-conjugation. They are good candidates for adjusting the band gap of organic polymer semiconducting materials. Thieno[3,2-b]thiophene-2-carbonitrile is used as an intermediate for the synthesis of small molecules and polymers in the application of organic field-effect transistors (OFETs), and as organic photovoltaic devices (OPV) interface layers as HTL or ETL materials.

Synthesis of 3,6-bis(thieno[3,2-b]thiophen-5-yl)-2,5-bispyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione with Thieno[3,2-b]thiophene-2-carbonitrile as starting material
Synthesis of 3,6-bis(thieno[3,2-b]thiophen-5-yl)-2,5-bispyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, using Thieno[3,2-b]thiophene-2-carbonitrile.

 

Literature and Reviews

  1.  Thieno[3,​2-​b]​thiophene-​diketopyrrolopyrrole-​containing polymers for high-​performance organic field-​effect transistors and organic photovoltaic devices, H. Bronstein et al., J. Am. Chem. Soc., 133 (10), 3272–3275 (2011), DOI: 10.1021/ja110619k.
  2. Alkyl Chain Extension as a Route to Novel Thieno[3,2-b]thiophene Flanked Diketopyrrolopyrrole Polymers for Use in Organic Solar Cells and Field Effect Transistors, I. Meager et al., Macromolecules, 46 (15), 5961–5967 (2013), DOI: 10.1021/ma401128s.
  3. Photocurrent Enhancement from Diketopyrrolopyrrole Polymer Solar Cells through Alkyl-Chain Branching Point Manipulation, I. Meager et al.,, J. Am. Chem. Soc., 135 (31), 11537–11540 ( 2013 ), DOI: 10.1021/ja406934j.
  4. Thieno[3,2-b]thiophene-Diketopyrrolopyrrole-Based Quinoidal Small Molecules: Synthesis, Characterization, Redox Behavior, and n-Channel Organic Field-Effect Transistors, C. Wang et al., Chem. Eur. J., 20, 13755 – 13761 (2014), DOI: 10.1002/chem.201403037.
  5. Bis(thienothiophenyl) Diketopyrrolopyrrole-Based Conjugated Polymers with Various Branched Alkyl Side Chains and Their Applications in Thin-Film Transistors and Polymer Solar Cells, J. Shin et al., ACS Appl. Mater. Interfaces, 7 (5), 3280–3288  (2015), DOI: 10.1021/am508026s.
  6. Correlation of structure and photovoltaic performance of benzo[1,2-b:4,5-b′]dithiophene copolymers alternating with different acceptors, J. Yu et al., New J. Chem., 39, 2248-2255 (2015), DIO: 10.1039/C4NJ02192D.


To the best of our knowledge the technical information provided here is accurate. However, Ossila assume no liability for the accuracy of this information. The values provided here are typical at the time of manufacture and may vary over time and from batch to batch.