3,3′,5,5′-Tetrabromo-2,2′-bithiophene (CAS 125143-53-5) is a bithiophene building block used to prepare semiconducting small molecules, oligomers, conjugated polymers and extended fused aromatic systems. Its structure consists of two thiophene rings linked at the 2,2′-positions, with each ring carrying bromine atoms at the 3- and 5-positions.
The four bromine sites make the compound a versatile handle for coupling, polymerization and cyclization. The 3,3′-bromides in particular allow ring fusion, giving flatter structures with greater conjugation, and the compound has served as a precursor to dithieno[3,2-b:2′,3′-d]pyrrole, dithienosilole and related derivatives. Sonogashira–Hagihara polymerization with ethynylbenzene monomers has produced microporous polymers with iodine vapour uptake of up to 345 wt%, and bithiophene-imide homopolymers derived from it show n-channel field-effect transistor behaviour.
Ossila supplies this material at >98% purity (1H NMR in CDCl3) as a light yellow to white/off-white powder or crystals, for research into OLED, OFET and organic photovoltaic materials.
- Synthesis of conjugated polymers and low band gap polymers for organic photovoltaics.
- Preparation of dithienopyrrole and dithienosilole fused-ring building blocks.
- Development of n-channel polymer semiconductors for organic field-effect transistors.
- Construction of conjugated microporous polymers for iodine vapour capture.
- Production of 3,3′-dibromobithiophene by reduction with zinc in hydrochloric and acetic acid.
| Brand | Ossila |
|---|---|
| CAS number | 125143-53-5 |
| Molecular formula | C8H2Br4S2 |
| Purity | >98% (1H NMR in CDCl3) |
| Category | — |
| Pack sizes | 10 g, 25 g, 50 g, 100 g |
| Physical form | Light yellow to white/off white powder/crystals |
| Storage | — |
- Product code: B1081
- Molecular Weight: 481.85 g/mol
- Synonym: 3,5-dibromo-2-(3,5-dibromo-2-thienyl)thiophene
- Melting Point: 144.0 °C
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