Description
2-Thiophenecarboxaldehyde, 5-[4-(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]- (CAS: 1858204-07-5) is a high-purity organic compound with the molecular formula C31H39BrN2O3S2. This specialized chemical features a unique pyrrolo[3,4-c]pyrrole core functionalized with bromothiophene and thiophenecarboxaldehyde moieties, making it a valuable intermediate for advanced materials research. Its bis(2-ethylhexyl) side chains enhance solubility in organic solvents, facilitating processing in thin-film applications. With a molecular weight of 631.68 g/mol, this compound is particularly relevant in the development of organic semiconductors, dye-sensitized solar cells (DSSCs), and other optoelectronic devices. Available in research quantities, it is supplied with comprehensive analytical data including 1H NMR, HPLC, and mass spectrometry to ensure quality and consistency for your experiments.
Properties
- CAS Number: 1858204-07-5
- Complexity: 983
- IUPAC Name: 5-[4-(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-3,6-dioxo-pyrrolo[3,4-c]pyrrol-1-yl]thiophene-2-carbaldehyde
- InChI: InChI=1S/C31H39BrN2O3S2/c1-5-9-11-20(7-3)17-33-28(23-14-13-22(19-35)38-23)26-27(31(33)37)29(24-15-16-25(32)39-24)34(30(26)36)18-21(8-4)12-10-6-2/h13-16,19-21H,5-12,17-18H2,1-4H3
- InChI Key: ITBLTAAYBUCTOQ-UHFFFAOYSA-N
- Exact Mass: 630.15855
- Molecular Formula: C31H39BrN2O3S2
- Molecular Weight: 631.7
- SMILES: CCCCC(CC)CN1C(=C2C(=C(N(C2=O)CC(CC)CCCC)C3=CC=C(S3)Br)C1=O)C4=CC=C(S4)C=O
- Topological: 114
- Monoisotopic Mass: 630.15855
- Synonyms: 1858204-07-5, 2-Thiophenecarboxaldehyde, 5-[4-(5-bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-2,3,5,6-tetrahydro-3,6-dioxopyrrolo[3,4-c]pyrrol-1-yl]-, DPP26-CHO-Br, MFCD34598484, 5-[4-(5-Bromo-2-thienyl)-2,5-bis(2-ethylhexyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl]thiophene-2-carbaldehyde, SY328277
Application
This compound serves as a key building block in the synthesis of donor-acceptor conjugated polymers for organic photovoltaics. Researchers utilize its electron-deficient pyrrolopyrrole dione (DPP) core to create low-bandgap materials with enhanced light absorption. The bromothiophene moiety enables further functionalization via cross-coupling reactions, while the aldehyde group provides an anchor for condensation reactions. Its applications extend to the development of near-infrared (NIR) dyes and as a precursor for small molecule organic semiconductors. The 2-ethylhexyl groups improve solution processability for spin-coating and inkjet printing applications.
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