Terthiophene

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title: "Terthiophene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["thiophenes"] topic_path: "general/thiophenes" source: "https://en.wikipedia.org/wiki/Terthiophene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | verifiedrevid = 470603009 | Name = Terthiophene | ImageFile = Alpha-Terthiophene numbering.svg | ImageName = Terthiophene | PIN = 12,22:25,32-Terthiophene | OtherNames = α-Terthienyl 2,5-Di(2-thienyl)thiophene |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 1081-34-1 | Beilstein = 178604 | ChEBI_Ref = | ChEBI = 10335 | ChEMBL_Ref = | ChEMBL = 90017 | ChemSpiderID_Ref = | ChemSpiderID = 58578 | EINECS = 640-441-1 | KEGG = C08460 | PubChem = 65067 | RTECS = WZ9717750 | UNII_Ref = | UNII = 0P77RAU2RR | InChI = 1/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H | InChIKey = KXSFECAJUBPPFE-UHFFFAOYAI | StdInChI_Ref = | StdInChI = 1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H | StdInChIKey_Ref = | StdInChIKey = KXSFECAJUBPPFE-UHFFFAOYSA-N | SMILES = s1cccc1c2sc(cc2)c3sccc3 |Section2={{Chembox Properties | Formula = C12H8S3 | MolarMass = 248.39 g/mol | Appearance = pale yellow solid | Density = | Solubility = insoluble | MeltingPt = 93-95 °C |Section3={{Chembox Structure | CrystalStruct = | Dipole = |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = flammable | GHS_ref= | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases = |Section8={{Chembox Related | OtherCompounds = Thiophene polythiophene

Terthiophene is the organic compound with the formula [C4H3S]2C4H2S. It is an oligomer of the heterocycle thiophene, a shorter oligomer is dithienyl, and the parent polymer is polythiophene. In the most common isomer of terthiophene, two thienyl groups are connected via their 2 positions to a central thiophene, also at the carbon atoms flanking the sulfur.

Preparation of terthiophene

Terthiophene is prepared by the nickel- or palladium-catalysed coupling reaction of 2,5-dibromothiophene with the Grignard reagent derived from 2-bromothiophene.

Properties and applications

This substance is likely responsible for the insecticidal activity of Tagetes minuta as it can react with light and oxygen to make singlet oxygen.{{Cite journal | last1 = Perich | first1 = M. J. | last2 = Wells | first2 = C. | last3 = Bertsch | first3 = W. | last4 = Tredway | first4 = K. E. | title = Isolation of the insecticidal components of Tagetes minuta (Compositae) against mosquito larvae and adults | journal = Journal of the American Mosquito Control Association | volume = 11 | issue = 3 | pages = 307–310 | year = 1995 | pmid = 8551298

Together with derivatives of 2,2'-bithiophene, various chlorinated terthiophenes occur naturally in thistles.

Terthiophene has been employed as building block for the organic semi-conductor polythiophene.

References

References

  1. "2,2':5',2"-Terthiophene".
  2. (2003). "Process Design and Scale-Up of the Synthesis of 2,2':5',2"-Terthienyl". Organic Process Research & Development.
  3. (1994). "Generation of singlet oxygen by 2,2':5',2"-terthiophene and some of its derivatives". Journal of Photochemistry and Photobiology A.
  4. (2002). "New thiophenes from ''Echinops grijisii''". Journal of Asian Natural Products Research.

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thiophenes