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

3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
Order Code: B241
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Note: This product has been used in our own lab by Ossila chemist for the synthesis of PDPP4Tand high mobility p-type polymer DPP-DTT.

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 

Product Details

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

 

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. CAS number 1260685-63-9. Chemical formula: C54H86Br2N2O2S2.

 

Applications

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

 

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).

 

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).

 

To the best of our knowledge the technical information provided here is accurate. However, Ossila assume no liability for the accuracy of this information. The values provided here are typical at the time of manufacture and may vary over time and from batch to batch.

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