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

CAS Number 469912-82-1

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers, Organotin Compounds

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

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

High-purity monomer used in organic electronic devices

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Specifications | MSDS | Literature and Reviews

2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene, CAS number 469912-82-1, 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.

Capped with trimethyltin

For facil coupling reactions

Thienothiophene building block

For semiconductors, OFETs, and solar cells

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High purity

>98% High purity

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

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 MSDS sheet

Literature and Reviews

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)
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)
Liquid-crystalline semiconducting polymers with high charge-carrier mobility, I. Mcculloch et al., Nat. Mater., 5, 328 (2006).

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).