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

Base Information

• Chemical Name: 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• CAS No.: 1260685-63-9
• Molecular Formula: C54H86Br2N2O2S2
• Molecular Weight: 1019.21
• Mol file: 1260685-63-9.mol

Synonyms:DPP‐iC20;

Chemical Property of 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Chemical Property:

• Melting Point: 95.0-96.9℃ (hexane toluene )
• Boiling Point: 925.3±65.0 °C(Predicted)
• PKA: -5.37±0.60(Predicted)
• PSA: 100.48000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 19.32980
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98% ^*data from raw suppliers

3,6-Bis(5-bromothien-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 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.
• Uses: 3,6-Bis(5-bromothien-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-dione is an intermediate in the synthesis of DPPT-TT which are organic thin-film transistors.

Technology Process of 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

There total 10 articles about 3,6-Bis(5-broMothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2,5-bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (1267540-02-2) → 3,6-bis(5-bromothiophene-2-yl) 22,5-bis(2-octyl-1-dodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1260685-63-9)

Guidance literature:

With N-Bromosuccinimide; In chloroform; at 20 ℃;

DOI:10.1021/ma401873s

Reference yield:

thiophene-2-carbonitrile (1003-31-2) → 3,6-bis(5-bromothiophene-2-yl) 22,5-bis(2-octyl-1-dodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1260685-63-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tert-pentoxide / tert-Amyl alcohol / 120 °C

2: potassium carbonate / N,N-dimethyl-formamide / 130 °C

3: bromine / chloroform / 20 °C

With bromine; sodium tert-pentoxide; potassium carbonate; In tert-Amyl alcohol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ja1085996

Reference yield:

2-octyldodecan-1-ol (5333-42-6,8039-11-0) → 3,6-bis(5-bromothiophene-2-yl) 22,5-bis(2-octyl-1-dodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1260685-63-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 120 °C

3: N-Bromosuccinimide / chloroform / 20 °C

With 1H-imidazole; N-Bromosuccinimide; iodine; potassium carbonate; triphenylphosphine; In dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/cm2037487

upstream raw materials:

thiophene-2-carbonitrile

2,5-bis(2-octyldodecyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

9-(iodomethyl)nonadecane

2-octyldodecan-1-ol

Downstream raw materials:

C₁₁₄H₁₆₄N₂O₈S₆