2,2′:5′,2′′-Terthiophene (CAS 1081-34-1), also called α-terthienyl, is an oligothiophene made of three thiophene rings linked through their α-positions. It serves as a starting material for building semiconducting small molecules, oligomers and conjugated polymers, and it is also a precursor for liquid crystalline materials. Ossila supplies it at >98% purity (1H NMR in CDCl3) as an off-white to orange-brown powder or crystals.
The compound can be made from 2,5-dibromothiophene through Kumada, Stille or Suzuki coupling, or by cyclization of 2-thienylacetylenes. Derivatives such as 5,5″-dicyano-2,2′:5′,2″-terthiophene, prepared from α-terthienyl, show liquid crystalline behaviour under polarizing optical microscopy, with molecular orientation in their crystalline phases.
In nature, α-terthienyl is a secondary metabolite abundant in marigold roots. When activated by ultraviolet light it is toxic to several insect species and can inhibit enzymes by generating oxygen radical species, which makes it of interest in insecticide and pesticide research.
- Synthesis of semiconducting molecules, oligomers and conjugated polymers, including low band gap polymers.
- Intermediate for materials used in OLEDs, OFETs and organic photovoltaics.
- Starting material for oligothiophene-based liquid crystals such as 5,5″-dicyano-2,2′:5′,2″-terthiophene.
- Research on UV-activated, plant-derived insecticides and pesticides.
| Brand | Ossila |
|---|---|
| CAS number | 1081-34-1 |
| Molecular formula | C12H8S3 |
| Purity | >98% (1H NMR in CDCl3) |
| Category | — |
| Pack sizes | 10 g, 25 g, 50 g |
| Physical form | Off-white to orange-brown powder/crystals |
| Storage | — |
- Product code: B1061
- Molecular Weight: 248.39 g/mol
- Synonyms: α-terthienyl, 2,5-Di(2-thienyl)thiophene
- Melting Point: 95.0 °C
- Classification / Family: Terthiophene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics
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