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

All Monomers, Thiophene, TT, BDT, BDD, FL & Cz

2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene chemical structure
Product Code B171-1g
Price $225 ex. VAT
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High-purity monomer used in organic electronic devices

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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

Note: This product has been used in our own lab by Ossila chemists 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

Chemical Structure

Chemical structure of 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene, CAS 469912-82-1
Chemical structure of 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene, CAS 469912-82-1

Product Details

Purity >98% (NMR)
Melting Point 128 °C - 131 °C
Appearance White crystals

Charaterisation

1H NMR bis-trimethylstannyl-thienothiophene
1H NMR spectrum of 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene in CDCl3 (view full version)

MSDS Documentation

2,5-bis(trimethylstannyl)-thieno[3,2-b]thiophene MSDS2,5-bis(trimethylstannyl)-thieno[3,2-b]thiophene MSDS sheet

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).

To the best of our knowledge the information provided here is accurate. However, Ossila assume no liability for the accuracy of this page. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only, and may not be used for any other purpose including health care, military, pharmaceuticals, cosmetics, food, or commercial applications.

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