Benzo[1,2-b:4,5-b']dithiophene-4,8-dione

Order Code: B261
MSDS sheet

Price

(excluding Taxes)

£67.00


General Information

CAS number
32281-36-0
Chemical formula C10H4O2S2
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

chemical structure of Benzo-dithiophene-dione cas number 32281-36-0
Chemical structure of Benzo[1,2-b:4,5-b']dithiophene-4,8-dione
CAS number 32281-36-0; Chemical formula C10H4O2S2

 

Applications

Benzo[1,2-b:4,5-b’]dithiophene, a planar symmetrical molecular structure of the thiophene derivative, enabling a better π-π stacking and good electron delocalization thus encourage charge transport, has been intensively studied for the application of OFETs and OPVs in the recent years. 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. Also Benzo[1,2-b:4,5-b’]dithiophene can be easily modified chemically to allow fine tuning the chemical structure and also the electron properties such as the bandgap, the energy level and charge mobilities of the small molecules or polymers of interest at 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 starting material.

synthesis of bis-2-ethylhexylthiophene-benzodithiophene using benzodithiophene as 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 Charaterisation

 

1H NMR of benzodithiophene-dionein CDCl3
1H NMR spectrum of Benzo[1,2-b:4,5-b']dithiophene-4,8-dione in CDCl3 (view full version)

Literature and Reviews

  1. 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)
  2. 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)
  3. 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)
  4. 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)
  5. 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)