General Information
CAS number 32281-36-0
Chemical formula C10 H4 O2 S2
Molecular weight 220.26 g/mol
Synonyms
Benzo[1,2-b:4,5-b']bisthiophene-4,8-dione
Thieno[2,3-f][1]benzothiophene-4,8-dione
Classification / Family Thiophenes, Monomers, Building blocks, Carbazoles, Heterocycles, Polymer synthesis, Semiconductor synthesis, Intermediates for high performance, Organic Photovoltaics
Product Details
Purity >99%
Melting point 260-263°C
Apperance
Yellow powder
Chemical structure of Benzo[1,2-b:4,5-b']dithiophene-4,8-dione. CAS number 32281-36-0; Chemical formula C10 H4 O2 S2 .
Applications
Benzo[1,2-b:4,5-b’]dithiophene is a planar symmetrical molecular structure of the thiophene derivative, enabling a better π-π stacking and good electron delocalization that encourages charge transport. In recent years, it has been intensively studied for the application of OFETs and OPVs. The incorporation of a low-band-gap unit into the benzo[1,2-b:4,5-b’]dithiophene unit could potentially result in a red-shifted absorption due to its electron-rich properties. Benzo[1,2-b:4,5-b’]dithiophene can be chemically modified to fine-tune its chemical structure and electron properties (e.g. band gap), energy levels, and charge mobility of the small molecule/polymers of interest (at a molecular level).
Benzo[1,2-b:4,5-b’]dithiophene (BDT) backboned polymers or small molecules thus provides a relatively better device performance. The following is a good example of a finely tuned structure being synthesised with Benzo[1,2-b:4,5-b’]dithiophene as a starting material.
Synthesis of 4,8-Bis(2-ethylhexylthiophene)-benzo[1,2-b:4,5-b′]dithiophene using 4,8-benzo[1,2-b:4,5-b′]dithiophene and 2-ethylhexylthiophene as starting materials.
NMR Characterisation
1 H NMR spectrum of Benzo[1,2-b:4,5-b']dithiophene-4,8-dione in CDCl3. (view full version )
Literature and Reviews
Utilizing alkoxyphenyl substituents for side-chain engineering of efficient benzo[1,2-b:4,5-b′]dithiophene-based small molecule organic solar cells, Z. Du, et al., Phys. Chem. Chem. Phys., 17, 17391-17398 (2015)
Thieno[3,2‑b]thiophene-Substituted Benzo[1,2‑b:4,5‑b′]dithiophene as a Promising Building Block for Low Bandgap Semiconducting Polymers for High-Performance Single and Tandem Organic Photovoltaic Cells, J-H. Kim, et al., Chem. Mater., 26, 1234−1242 (2014)
New Benzo[1,2-b:4,5-b’]dithiophene-Based Small Molecules Containing Alkoxyphenyl Side Chains for High Efficiency Solution-Processed Organic Solar Cells , Z. Du, et al., ChemSusChem, 7, 3319 – 3327 (2014)
Polybenzo[1,2-b:4,5-b’]dithiophene Derivative with Deep HOMO Level and Its Application in High-Performance Polymer Solar Cells, L. Huo et al., Angew. Chem. Int. Ed., 49, 1500 –1503 (2010)
Bandgap and Molecular Energy Level Control of Conjugated Polymer Photovoltaic Materials Based on Benzo[1,2-b:4,5-b′]dithiophene, J. Hou et al., Macromolecules, 41, 6012-6018 (2008)
