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

Order Code: B211

Price

(excluding Taxes)

£261.50


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

 

Product Details

Purity

>98%

Melting point

 Not data available

Appearance Yellow oil

 

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 number 365547-21-3; Chemical formula C25H36Br2S2

 

Applications

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 lowers the 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

 NMR Charaterisation

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)

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)