Description

3,6-Bis(5-bromothiophen-2-yl)-2,5-bis(4-octyltetradecyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (CAS: 2116427-63-3) is a high-purity, brominated thiophene-functionalized diketopyrrolopyrrole (DPP) derivative with the molecular formula C₅₈H₉₄Br₂N₂O₂S₂. This advanced organic semiconductor material features a rigid, planar DPP core flanked by bromothiophene units, enhancing its optoelectronic properties and solubility due to the branched 4-octyltetradecyl side chains. Ideal for researchers developing organic electronics, this compound exhibits excellent charge transport characteristics, broad absorption spectra, and tunable energy levels, making it suitable for organic field-effect transistors (OFETs), organic photovoltaics (OPVs), and perovskite solar cells. Supplied as a dark solid with >95% purity (HPLC), it is rigorously characterized by ¹H/¹³C NMR, MS, and elemental analysis. Store under inert conditions at -20°C to ensure long-term stability.

Properties

• CAS Number: 2116427-63-3
• Complexity: 1290
• IUPAC Name: 1,4-bis(5-bromo-2-thienyl)-2,5-bis(4-octyltetradecyl)pyrrolo[3,4-c]pyrrole-3,6-dione
• InChI: InChI=1S/C58H94Br2N2O2S2/c1-5-9-13-17-21-23-27-31-37-47(35-29-25-19-15-11-7-3)39-33-45-61-55(49-41-43-51(59)65-49)53-54(57(61)63)56(50-42-44-52(60)66-50)62(58(53)64)46-34-40-48(36-30-26-20-16-12-8-4)38-32-28-24-22-18-14-10-6-2/h41-44,47-48H,5-40,45-46H2,1-4H3
• InChI Key: WPGNZENRDPPLQG-UHFFFAOYSA-N
• Exact Mass: 1074.51030
• Molecular Formula: C58H94Br2N2O2S2
• Molecular Weight: 1075.3
• SMILES: CCCCCCCCCCC(CCCCCCCC)CCCN1C(=C2C(=C(N(C2=O)CCCC(CCCCCCCC)CCCCCCCCCC)C3=CC=C(S3)Br)C1=O)C4=CC=C(S4)Br
• Topological: 97.1
• Monoisotopic Mass: 1072.51235
• Synonyms: 2116427-63-3, 3,6-Bis(5-bromothiophen-2-yl)-2,5-bis(4-octyltetradecyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

Application

This brominated DPP derivative is widely used in the synthesis of low-bandgap polymers for high-performance organic solar cells, leveraging its strong electron-withdrawing properties and extended conjugation. Its bromine substituents enable efficient cross-coupling reactions (e.g., Stille, Suzuki) for π-conjugated polymer design. Researchers also employ it as an n-type semiconductor in OFETs due to its high electron mobility (>0.1 cm²/V·s). Additionally, it serves as a key building block for near-infrared (NIR) dyes and non-fullerene acceptors in tandem photovoltaic devices.

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