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3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

CAS Number 1260685-63-9

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione CAS 1260685-63-9
Product Code B241-1g
Price $338 ex. VAT
$ USD

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High purity monomer, used to optimise the performance of organic semiconductors

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Specifications | MSDS | Literature and Reviews

The monomer, 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, CAS Number 1260685-63-9, contains a DPP moiety. DPP backbone derivatives as a strong acceptor unit, have a planar conjugated bicyclic structure engaging stronger π–π interactions which allows tuning the band-gap and energy-level of polymer organic semiconductors. Also long alkyl chains, namely 2-octyldodecyl, will allow better solubility for the polymer semiconductor and crystallization and aggregation capacity for the thin-film devices. DPP-containing polymers are considered promising materials for optimizing the performance of organic semiconductors.

2,5-Bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione-based donor-acceptor alternating copolymer bearing 5,5'-di(thiophen-2-yl)-2,2'-biselenophene exhibiting 1.5 cm2/Vs hole mobility in thin-film transistors.

pdpp-alt-dtbse-synthesis with 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione and 5,5’-di(thiophen-2-yl)-2,2’-biselenophene
PDPP-alt-DTBSe synthesis with 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione and 5,5’-di(thiophen-2-yl)-2,2’-biselenophene via Stille Coupling polymerisation

Note: This product has been used in our own lab by Ossila chemist for the synthesis of PDPP4T and high mobility p-type polymer DPP-DTT.

Capped with bromide

Capped with bromide

A DPP-DTT monomer

Pyrrolopyrrole building block

Pyrrolopyrrole building block

For semiconductors, OFETs, and solar cells

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High purity 1260685-63-9

High purity

>98% High purity

General Information

CAS Number 1260685-63-9
Chemical Formula C54H86Br2N2O2S2
Molecular Weight 1019.2 g/mol
Synonyms
  • 3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-octyldodecyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
  • 3,6-Bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-bis(2-octyldodecyl)-pyrrolo[3,4-c]pyrrole-1,4-dione
  • 3,6-bis-(5-bromo-thiophen-2-yl)-N,N'-bis(2-octyldodecyl)-1,4-dioxo-pyrrolo[3,4-c]pyrrole
  • DPP-OD-2ThBr
Classification / Family Pyrroles, Thiophenes, Acceptor, Organic semiconducting materials, Semiconductor synthesis, Building blocks

Chemical Structure

chemical structure of bisbromothiophenyl-bisoctyldodecylpyrrolo-dione cas number 1260685-63-9
Chemical structure of 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Product Details

Purity >98%
Melting Point 95 °C - 97 °C
Appearance Dark purple solid

NMR Characterisation

1H NMR 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
1H NMR spectrum of 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione in CDCl3: Instrument AVIIIHD400 (see full version)

MSDS Documentation

DPP-OD-2ThBr MSDSDPP-OD-2ThBr MSDS sheet

Literature and Reviews

  1. Effect of Selenophene in a DPP Copolymer Incorporating a Vinyl Group for High-Performance Organic Field-Effect Transistors, I. Kang et al., Adv. Mater., 25, 524-528 (2013).
  2. Synthesis, Characterization, and Field-Effect Transistors Properties of Novel Copolymers Incorporating Nonplanar Biindeno[2,1-b]thiophenylidene Building Blocks, C. Li, Macromolecules, 48 (8), 2444-2453 (2015).
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