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

Price

(excluding Taxes)

£239.60

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
Classification / Family Pyrroles, Thiophenes, Acceptor, Organic semiconducting materials, Semiconductor synthesis, Building blocks 

 

Product Details

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

 

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. 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).