Description

6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2′,3′-d’]-s-indaceno[1,2-b:5,6-b’]dithiophene-2,8-dibromo (CAS: 2227361-27-3) is a high-purity, brominated organic semiconductor compound with the molecular formula C₆₈H₇₂Br₂S₄. This advanced material features a complex fused-ring structure with four hexylphenyl substituents, enhancing solubility and processability while maintaining excellent charge-transport properties. The dibromo functionalization at the 2,8-positions makes it a valuable intermediate for further cross-coupling reactions in the synthesis of conjugated polymers and small molecules. With its extended π-conjugation and electron-rich heterocyclic core, this compound is particularly suited for applications in organic electronics, including organic field-effect transistors (OFETs) and organic photovoltaics (OPVs). Supplied as a stable solid with rigorous quality control, this specialty chemical is ideal for researchers developing next-generation optoelectronic materials.

Properties

• CAS Number: 2227361-27-3
• Complexity: 1500
• IUPAC Name: 8,20-dibromo-12,12,24,24-tetrakis(4-hexylphenyl)-5,9,17,21-tetrathiaheptacyclo[13.9.0.03,13.04,11.06,10.016,23.018,22]tetracosa-1(15),2,4(11),6(10),7,13,16(23),18(22),19-nonaene
• InChI: InChI=1S/C68H72Br2S4/c1-5-9-13-17-21-45-25-33-49(34-26-45)67(50-35-27-46(28-36-50)22-18-14-10-6-2)55-41-54-56(42-53(55)63-61(67)65-57(71-63)43-59(69)73-65)68(62-64(54)72-58-44-60(70)74-66(58)62,51-37-29-47(30-38-51)23-19-15-11-7-3)52-39-31-48(32-40-52)24-20-16-12-8-4/h25-44H,5-24H2,1-4H3
• InChI Key: XITWEJRNSOCYSJ-UHFFFAOYSA-N
• Exact Mass: 1176.28631
• Molecular Formula: C68H72Br2S4
• Molecular Weight: 1177.4
• SMILES: CCCCCCC1=CC=C(C=C1)C2(C3=CC4=C(C=C3C5=C2C6=C(S5)C=C(S6)Br)C(C7=C4SC8=C7SC(=C8)Br)(C9=CC=C(C=C9)CCCCCC)C1=CC=C(C=C1)CCCCCC)C1=CC=C(C=C1)CCCCCC
• Topological: 113
• Monoisotopic Mass: 1174.28836
• Synonyms: 2227361-27-3, 6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2′,3′-d’]- s-indaceno[1,2-b:5,6-b’]dithiophene-2,8-dibromo, 6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2′,3′-d’]-s-indaceno[1,2-b:5,6-b’]dithiophene-2,8-dibromo

Application

This dibrominated indacenodithiophene derivative serves as a key building block for synthesizing high-performance conjugated polymers used in organic electronic devices. Its extended π-system and bromine substituents enable efficient polymerization via Stille or Suzuki coupling reactions, yielding materials with tailored bandgaps for photovoltaic applications. The compound’s hexylphenyl side chains promote solution processability while maintaining solid-state order, making it valuable for fabricating thin-film transistors with high charge carrier mobility. Researchers also utilize this intermediate to develop donor-acceptor copolymers for bulk heterojunction solar cells, where its electron-rich structure enhances light absorption and hole transport.

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