5,5'-bis(trimethylstannyl)-2,2'-bithiophene


Order Code: B221
Not in stock

Note: This product has been used in our own lab by Ossila chemist for the synthesis of PDPP4T and DPPDPyBT (n-type).

General Information

CAS number 143367-56-0
Chemical formula C14H22S2Sn2
Molecular weight 491.87 g/mol
Synonyms 5,5-Ditrimethylstannyl-2,2'-bithiophene
5,5'-Bis(trimethyltin)-2,2'-bithiophene
Classification / Family Bithiophene, Thiophene, Heterocyclic five-membered ring, Organic semiconducting materials, Semiconductor Synthesis, Low band gap polymers, OFETs, OLED, Organic Photovoltaics, Polymer Solar Cells

 

Product Details

Purity

>97%

Melting point

96-100°C

Appearance White flakes
Chemical structure of 5,5'-bis(trimethylstannyl)-2,2'-bithiophene< CAS number 143367-56-0; Chemical formula C14H22S2Sn2.

 

Applications

5,5'-bis(trimethylstannyl)-2,2'-bithiophene can be used for the synthesis of small molecules and polymer semiconductors for OFETs, OLED, PLED, OPV applications.5,5'-bis(trimethylstannyl)-2,2'-bithiophene can be prepared from 2,2'-bithiophene which is an electron rich and donating unit if it is embedded into low band-gap polymer semiconductors.

Reacting with 4,​9-​dibromo-​2,​7-​bis(2-​octyldodecyl)​-Benzo[3,​8]​phenanthroline-​1,​3,​6,​8-(2H,​7H)​-​tetrone, 5,5'-bis(trimethylstannyl)-2,2'-bithiophene yields a heavily n-dopable π-conjugated redox polymer, poly{[N,N′-bis(2-octyldodecyl)-1,4,5,8-naphthalenedicarboximide-2,6-diyl]-alt-5,5′-(2,2′-bithiophene)} (PNDI2OD-T2).

 

Synthesis of PNDI2OD-T2 by reacting 4,9-dibromo-2,7-bis(2-octyldodecyl)-Benzo[3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone with 5,5'-bis(trimethylstannyl)-2,2'-bithiophene via Stille Coupling polymerisation

 

Characterisation

 

1H NMR bistrimethylstannylbithiophene in CDCl3 1H NMR spectrum of 5,5'-bis(trimethylstannyl)-2,2'-bithiophene in CDCl3; 400 MHz spectrometer.

 

Literature and Reviews

  1. A Polythiophene Derivative with Superior Properties for Application in Polymer Solar Cells, M. Zhang, Adv. Mater., 26 (33), 5880-5885 (2014)
  2. Low Band-Gap Conjugated Polymers with Strong Interchain Aggregation and Very High Hole Mobility Towards Highly Efficient Thick-Film Polymer Solar Cells, Z. Chen, Adv. Mater., 26 (16), 2586-2591 (2014)
  3. A high-mobility electron-transporting polymer for printed transistors, H. Yan, Nat. Mater., 457, 679 (2009)
  4. Bithiophene-Imide-Based Polymeric Semiconductors for Field-Effect Transistors: Synthesis, Structure-Property Correlations, Charge Carrier Polarity, and Device Stability, X. Guo et al., J. Am. Chem. Soc., 133, 1405-1418 (2011)

 


To the best of our knowledge the technical information provided here is accurate. However, Ossila assume no liability for the accuracy of this information. The values provided here are typical at the time of manufacture and may vary over time and from batch to batch.