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

Order Code: B221

Price

(excluding Taxes)

£79.00


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

Color White flakes

 

Chemical Structure

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

 NMR Charaterisation

1H NMR bistrimethylstannylbithiophene in CDCl3
1H NMR spectrum of 5,5'-bis(trimethylstannyl)-2,2'-bithiophene in CDCl3: Instrument AVIIIHD400 (see full version)

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)