4,7-Dibromo-2,1,3-benzothiadiazole

Order Code: B101

Price

(excluding Taxes)

£66.00


General Information

CAS number 15155-41-6
Chemical formula C6H2Br2N2S
Molecular weight 293.97 g/mol
Synonyms

Dibromo Benzothiodiazole

Dibromo-BT

Classification / Family

Benzothiodiazole, PCPDTBT

Semiconductor Synthesis, Low band gap polymers, Acceptors

Organic Photovoltaics, Polymer Solar Cells

 

Product Details

Purity

>95%

Melting point

187-190°C

Color Light yellow crystals

 

Chemical Structure

chemical structure of dibromobenzothiadiazole cas number 15155-41-6
Chemical structure of 4,7-Dibromo-2,1,3-benzothiadiazole
CAS number 15155-41-6; Chemical formula C6H2Br2N2S

 

Applications

4,7-Dibromo-2,1,3-benzothiadiazole is the building block or monomer for organic semiconductors synthesis in the application of light-emitting diodes and photovoltaic devices. Intermediate for the synthesis of i.e. PCDTBT and PCPDTBT.

4,7-Dibromo-2,1,3-benzothiadiazole can be synthesised by using 2,1,3-benzothiadiazole as starting materials to react with bromine in hydrobromic acid. Further bromination of 4,7-Dibromo-2,1,3-benzothiadiazole affords 4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazole, a red monomer leading to our pilot polymer PCDTBT which can be used for OPV devices. 4,7-Dibromo-2,1,3-benzothiadiazole is also used for the synthesis of PCPDTBT, a good candidate for the polymer solar cell devices.

dibromo thienyl benzothiadiazole synthesis with benzothiadiazole via dibromo benzothiadiazole
Synthesis of 4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazole from 2,1,3-benzothiadiazole via 4,7-Dibromo-2,1,3-benzothiadiazole

 

NMR Characterisation

1H NMR of Dibromo-benzothiadiazole in CDCl3

1H NMR spectrum of 4,7-Dibromo-2,1,3-benzothiadiazole in CDCl3: Instrument AVIIIHD400 (see full version)

Literature and Reviews

  1. Introduction of Perylene Units for Enhanced Interchain Interaction in Conjugated Polymers for Organic Photovoltaic Devices, K. Ji-Hoon et al., Macromolecules, 45(5), 2367-2376 (2012)
  2. Fluorinated Copolymer PCPDTBT with Enhanced Open-Circuit Voltage and Reduced Recombination for Highly Efficient Polymer Solar Cells, S. Albrecht et al., J. Am. Chem. Soc., 134, 14932-14944 (2012)