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2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene

CAS Number 365547-21-3

Chemistry Building Blocks, Dibromo Monomers, Heterocyclic Building Blocks, Monomers


Product Code B211-1g
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High-quality monomer that allows more effective conjugation

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2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene, with two thiophene units confined to one plane, cyclopenta[2,1-b;3,4-b′]dithiophene compounds allow more effective conjugation if embedded into semiconducting polymers which in turn will have a lower band gap. Furthermore, the planar structure will have greater effect on the morphology for the thin film devices to allow a well packed polymer to polymer backbones which will bring the third-dimension into play. Take PCPDTBT for example, the planar structure improves the hole mobility of the device to 1 x 10-3 cm2/Vs.

2,6-dibromo-4,4-bis(2-ethylhexyl)-4Hcyclopenta[1,2-b:5,4-b']dithiophene can be targeted by reacting 4,4-bis(2-ethylhexyl)-4Hcyclopenta[1,2-b:5,4-b']dithiophene with N-Bromosuccinimide in dimethylformamide.

synthesis of 2,6-dibromo-4,4-bis(2-ethylhexyl)-4Hcyclopenta[1,2-b:5,4-b']dithiophene using 4,4-bis(2-ethylhexyl)-4Hcyclopenta[1,2-b:5,4-b']dithiophene
Synthesis of 2,6-dibromo-4,4-bis(2-ethylhexyl)-4Hcyclopenta[1,2-b:5,4-b']dithiophene using 4,4-bis(2-ethylhexyl)-4Hcyclopenta[1,2-b:5,4-b']dithiophene and N-Bromosuccinimide in dimethylformamide.
Capped with bromide

Capped with bromide

a PCPDTBT monomer

Dithiophene building block

Dithiophene building block

for semiconductors, OFETs, and solar cells

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High purity 365547-21-3

High purity

>98% High purity

General Information

CAS Number 365547-21-3
Chemical Formula C25H36Br2S2
Molecular Weight 560.49 g/mol
Synonyms 2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-thieno[3',2':4,5]cyclopenta[1,2-b]thiophene
2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene
Classification / Family Dithiophene, Cyclopentadithiophene, Organic semiconducting materials, Semiconductor synthesis, Building blocks

Chemical Structure

chemical structure of dibromo-bis-ethylhexyl-4H-cyclopenta-dithiophene cas number 365547-21-3
Chemical structure of 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene, CAS 365547-21-3

Product Details

Purity >98%
Melting Point N/A
Appearance Yellow oil

NMR Characterisation

1 H NMR spectrum of 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene in CDCl3
1H NMR spectrum of 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene in CDCl3: Instrument AVIIIHD400 (see full version)

MSDS Documentation

2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene MSDS2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene MSDS Sheet

Literature and Reviews

  1. Cyclopentadithiophene-benzothiadiazole oligomers and polymers; synthesis, characterisation, field-effect transistor and photovoltaic characteristics, M. Horie et al., J. Mater. Chem., 22, 381 (2012)
  2. Copolymers of Cyclopentadithiophene and Electron-Deficient Aromatic Units Designed for Photovoltaic Applications, J.C. Bijleveld et al., Adv. Funct. Mater., 19, 3262-3270 (2009)
  3. Synthesis and Characterization of Bridged Bithiophene-Based Conjugated Polymers for Photovoltaic Applications: Acceptor Strength and Ternary Blends, C.-H. Chen, Macromolecules, 43 (2), 697-708 (2010)

To the best of our knowledge the information provided here is accurate. 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.

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