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

Order Code: B281
MSDS sheet

Price

(excluding Taxes)

£139.00


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

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 the organic polymer semiconducting materials. Thieno[3,2-b]thiophene-2-carbonitrile used as a intermediates for the synthesis of small molecules and polymers in the application of organic field-effect transistors (OFETs) and 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.