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Bromothiophene Benzothiadiazole

CAS Number 288071-87-4

Chemistry Building Blocks, Dibromo Monomers, Heterocyclic Building Blocks, Monomers


Product Code B121-1g
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Bromothiophene Benzothiadiazole, high purity red monomer

Used for the synthesis of semiconducting polymers


4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazole is a red monomer used for the synthesis of polymer semiconductors i.e. PCDTBT in the application of photovoltaic solar cell devices.

4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazole can be targeted by reacting 4,7-Dibromo-2,1,3-benzothiadiazole with N-Bromosuccinimide (NBS) in dichlorobenzene. Further reaction of the red monomer with 9-(heptadecan-9-yl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9Hcarbazole to afford PCDTBT.

PCDTBT synthesis carbazole boronic ester and dibromo-thienylbenzothiadiazole
Synthesis of PCDTBT with 4,7-bis(5-bromothiophen-2-yl) benzo[c][1,2,5]thiadiazole and 9-(heptadecan-9-yl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9Hcarbazole

Note: This product has been used in our lab for the synthesis of PCDTBT with device performance of 6.7% PCE.

Capped with bromide

Capped with bromide

a PCDTBT monomer

Benzothiadiazole building block

Benzothiadiazole building block

for semiconductors, OFETs, and solar cells

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High purity 288071-87-4

High purity

>98% High purity

General Information

CAS Number 288071-87-4
Chemical Formula C14H6Br2N2S3
Molecular Weight 458.21 g/mol
Synonyms Bromothiophene benzothiadiazole
4,7-Bis(5-bromo-2-thienyl)-2,1,3-benzothiadiazole
Classification / Family Benzothiadiazole, Bromothiophene, Semiconductor synthesis, Low band gap polymers, Acceptors, Organic Photovoltaics, Polymer solar cells

Chemical Structure

Bromothiophene-benzothiadiazole chemical structure
Chemical structure of 4,7-bis(5-bromothiophen-2-yl) benzo[c][1,2,5]thiadiazole

Product Details

Purity >98%
Melting Point 245 °C - 247 °C
Appearance Red needles / powder

Charaterisation

1H NMR dibromothienylbenzothiadiazole in CDCl3
1H-NMR spectrum of 4,7-bis(5-bromothiophen-2-yl) benzo[c][1,2,5]thiadiazole in CDCl3: Instrument AVIIIHD400 (see full version)

MSDS Documentation

4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazole MSDS4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazole MSDS sheet

Literature and Reviews

  1. Molecular weight dependent vertical composition profiles of PCDTBT:PC71BM blends for organic photovoltaics, J.W. Kingsley et al., Sci. Reports, 4, 5286 (2014)
  2. Bulk heterojunction solar cells with internal quantum efficiency approaching 100%, S. Park et al., Nat. Photonics, 3, 297-302 (2009)

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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