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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, Materials, Monomers

2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene CAS 365547-21-3
Product Code B211-1g
Price $351 ex. VAT
$ USD

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High-quality monomer that allows more effective conjugation

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Specifications | MSDS | Literature and Reviews

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