Description

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) is a high-purity, brominated thiophene-functionalized pyrrolopyrroledione derivative with the molecular formula C₅₄H₈₆Br₂N₂O₂S₂. This advanced organic semiconductor material features a rigid, planar π-conjugated core with electron-withdrawing dione groups, flanked by solubilizing 2-octyldodecyl chains for enhanced processability. The brominated thiophene moieties serve as versatile handles for further cross-coupling reactions, making this compound particularly valuable for synthesizing donor-acceptor polymers and small molecules in organic electronics. Supplied as a dark solid with >95% purity (HPLC), it is rigorously characterized by ¹H/¹³C NMR, mass spectrometry, and elemental analysis. Store under inert atmosphere at -20°C protected from light.

Properties

• CAS Number: 1260685-63-9
• Complexity: 1220
• IUPAC Name: 1,4-bis(5-bromo-2-thienyl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• InChI: InChI=1S/C54H86Br2N2O2S2/c1-5-9-13-17-21-23-27-31-35-43(33-29-25-19-15-11-7-3)41-57-51(45-37-39-47(55)61-45)49-50(53(57)59)52(46-38-40-48(56)62-46)58(54(49)60)42-44(34-30-26-20-16-12-8-4)36-32-28-24-22-18-14-10-6-2/h37-40,43-44H,5-36,41-42H2,1-4H3
• InChI Key: MULORLONPRJAON-UHFFFAOYSA-N
• Exact Mass: 1018.44770
• Molecular Formula: C54H86Br2N2O2S2
• Molecular Weight: 1019.2
• SMILES: CCCCCCCCCCC(CCCCCCCC)CN1C(=C2C(=C(N(C2=O)CC(CCCCCCCC)CCCCCCCCCC)C3=CC=C(S3)Br)C1=O)C4=CC=C(S4)Br
• Topological: 97.1
• Monoisotopic Mass: 1016.44975
• Synonyms: 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, 891-318-6, 1260685-63-9, Pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-bis(2-octyldodecyl)-, 1,4-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-3,6-dione, 3,6-Bis(5-bromothien-2-yl)-2,5-bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-Bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyldodecyl)-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione, MFCD27923046, SCHEMBL9961329, DTXSID90856412, AC-33729, BS-49898, CS-0196638, 3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-octyl-1-dodecyl)pyrrolo[3,4-c]pyrrole-1,4-dione

Application

This brominated DPP derivative is extensively used as a key intermediate in the synthesis of low-bandgap conjugated polymers for organic photovoltaics (OPVs) and field-effect transistors (OFETs). The compound serves as an electron-deficient building block in donor-acceptor copolymers when coupled with thiophene or selenophene donors via Stille or Suzuki cross-coupling. Researchers utilize its solution-processability to develop high-performance semiconductor materials with tunable energy levels. The bromine substituents enable precise structural modifications for optimizing charge transport properties in thin-film devices.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statements

• P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)

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