|Classification / Family
||Thiophene, Thienothiophene, Fused thiophene, Heterocyclic five-membered ring, Organic materials, Semiconductor synthesis, Low band gap polymers, OFETs, Organic photovoltaics, Polymer solar cells
|| 48-50 °C
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.
Literature and Reviews
- 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.
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.
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.
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.
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.
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.