2,1,3-Benzothiadiazole-4,7-bis(boronic acid pinacol ester)

Order Code: B181

Price

(excluding Taxes)

£79.00


General Information

CAS number 934365-16-9
Chemical formula C18H26B2N2O4S
Molecular weight 388.10 g/mol
Synonyms

2,1,3-Benzothiadiazole-4,7-diboronic acid bis(pinacol) ester

Benzo[c]-1,2,3-thiadiazol-4,7-diyl-4,7-diboronic acid dipinacol ester

4,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole

4,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

Classification / Family

Benzothiadiazole, Heterocyclic five-membered ring, Organic semiconducting materials.

Semiconductor Synthesis, Low band gap polymers, OFETs

OLED, Organic Photovoltaics, Polymer Solar Cells

 

Product Details

Purity

>98%

Melting point

213-215°C

Color White/Off-white powder

 

Chemical Structure

chemical structure of benzothiadiazole bisboronic acid pinacol ester cas number 934365-16-9
Chemical structure of 2,1,3-Benzothiadiazole-4,7-bis(boronic acid pinacol ester)
CAS number 934365-16-9; Chemical formula C18H26B2N2O4S

 

2,1,3-Benzothiadiazole-4,7-bis(boronic acid pinacol ester) is an intermediate for the synthesis of small molecules, oligomers and polymers via Suzuki Coupling reactions. Those small molecules, oligmomers and polymers can be printed, spray-coated or spin-coated onto devices for Organic Light-Emitting Diodes (OLED/PLED), Organic Field-Effect Transistors and Organic Photovoltaic devices.

2,1,3-Benzothiadiazole unit is electron deficient so it is employed for the low-band gap semiconducting materials used for OLED and OPV devices, i.e. F8BT and PCPDTBT.

Synthesis of PCPDTBT from benzothiadiazole boronic ester
Synthesis of PCPDTBT from the benzothiadiazole boronic ester and 2,6-dibromo-4,4-bis(2-ethylhexyl)-4Hcyclopenta[1,2-b:5,4-b']dithiophene

 

NMR Characterisation

 

1H NMR of fluorene-pinacol-ester in CDCl3
1H NMR spectrum of 2,1,3-Benzothiadiazole-4,7-bis(boronic acid pinacol ester) in CDCl3: Instrument AVIIIHD400 (view full version)

Literature and Reviews

  1. Combination of Molecular, Morphological, and Interfacial Engineering to Achieve Highly Efficient and Stable Plastic Solar Cells, C-Y. Chang et al, Adv. Mater., 24, 549-553 (2014)
  2. Development of Polymer Acceptors for Organic Photovoltaic Cells, Y. Kim et al., Polymers, 6, 382-407 (2014).