2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene

Order Code: B171

Price

(excluding Taxes)

£129.00


Note: This product has been used in our own lab by Ossila chemist for the synthesis of DPP-DTT (high mobility p-type polymer), one of our most popular products for optoelectronic devices.

General Information

CAS number 469912-82-1
Chemical formula C12H20S2Sn2
Molecular weight 465.84 g/mol
Synonyms

Stannane, 1,1'-thieno[3,2-b]thiene-2,5-diylbis(1,1,1-trimethyl)

Thieno[3,2-b]thien-2,5-diylbis(trimethylstannan)

Thieno[3,2-b]thiene-2,5-diylbis(trimethylstannane)

2,5-bis(trimethyltin)thieno[3,2-b]thiophene

Classification / Family

Thiophene, thienothiophene, Fused thiophene, Heterocyclic five-membered ring, Organic materials

Semiconductor Synthesis, Low band gap polymers, OFETs

Organic Photovoltaics, Polymer Solar Cells

 

Product Details

Purity

>98%

Melting point

128-131°C

Color White Crystals

 

Chemical Structure

chemical structure of trimethylstannyl thienothiophene
Chemical structure of 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene
CAS number 469912-82-1; Chemical formula C12H20S2Sn2

 

Applications

2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene can be prepared by using thieno[3,2-b]thiophene as starting material, further reaction with dibromo compounds (Stille Coupling) to form oligomers or polymers which can be used for organic electronic devices.

Thienothiophene is fused with extend conjugation over two thiophene rings. Thienothiophene is proven to be a good candidate for the materials that are used for Organic Field Effect Transistors, Sensors and OPV devices. Thienothiophene provide further tuning of energy gap of polymer materials with higher electron density over the conjugated ring systems.

dppt-co-tt synthesis with 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene and  3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
DPPT-co-TT synthesis with 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene and 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione via Stille Coupling polymerisation

 NMR Charaterisation

 

1H NMR bis-trimethylstannyl-thienothiophene
1H NMR spectrum of 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene in CDCl(view full version)

Literature and Reviews

  1. A High Mobility P-Type DPP-Thieno[3,2-b]thiophene Copolymer for Organic Thin-Film Transistors, Y. Li et al., Adv. Mater., 22, 4862-4866 (2010)
  2. Thieno[3,2-b]thiophene-Bridged D−π–A Polymer Semiconductor Based on Benzo[1,2-b:4,5-b′]dithiophene and Benzoxadiazole, X. Wang et al., Macromolecules, 46 (12), 4805-4812 (2013)
  3. Liquid-crystalline semiconducting polymers with high charge-carrier mobility, I. Mcculloch et al., Nat. Mater., 5, 328 (2006).
  4. Thieno[3,2-b]thiophene-Substituted Benzo[1,2-b:4,5-b′]dithiophene as a Promising Building Block for Low Bandgap Semiconducting Polymers for High-Performance Single and Tandem Organic Photovoltaic Cells, J-H. Kim et al., Chem. Mater., 26 (2), 1234–1242 (2014).