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

Order Code: B121

Price

(excluding Taxes)

£165.00


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

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

 

Product Details

Purify >98%
Melting point 245-247°C
Color Red needles / powder

 

Chemical Structure


Bromothiophene-benzothiadiazole
Chemical structure of 4,7-bis(5-bromothiophen-2-yl) benzo[c][1,2,5]thiadiazole
CAS number 288071-87-4; Chemical formula C14H6Br2N2S3

Applications

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

 NMR 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)

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)