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Terthiophene

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Terthiophene
Terthiophene
Names
Preferred IUPAC name 1,2:2,3-Terthiophene
Other names α-Terthienyl
2,5-Di(2-thienyl)thiophene
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 178604
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.168.218 Edit this at Wikidata
EC Number
  • 640-441-1
KEGG
PubChem CID
RTECS number
  • WZ9717750
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8HKey: KXSFECAJUBPPFE-UHFFFAOYSA-N
  • InChI=1/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8HKey: KXSFECAJUBPPFE-UHFFFAOYAI
SMILES
  • s1cccc1c2sc(cc2)c3sccc3
Properties
Chemical formula C12H8S3
Molar mass 248.39 g/mol
Appearance pale yellow solid
Melting point 93-95 °C
Solubility in water insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards flammable
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds Thiophene
polythiophene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Terthiophene is the organic compound with the formula 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 isomer is a pigment in African marigolds (Tagetes spp.) and exhibits some biological activity because it sensitizes the formation of singlet oxygen. It is responsible for the insecticidal activity of Tagetes minuta.

Together with derivatives of 2,2'-bithiophene, various substituted terthiophenes occur naturally. Examples include 5,5''-dichloro-α-terthiophene, 5-chloro-α-terthiophene, 5-acetyl α-terthiophene, and 5-carboxyl bithiophene.

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

See also

References

  1. "2,2':5',2"-Terthiophene". pubchem.ncbi.nlm.nih.gov.
  2. Smeets, B. J. J.; Meijer, R. H.; Meuldijk, J.; Vekemans, J. A. J. M. & Hulshof, L. A. (2003). "Process Design and Scale-Up of the Synthesis of 2,2':5',2"-Terthienyl". Organic Process Research & Development. 7 (1): 10–16. doi:10.1021/op020044n.
  3. Ciofalo, M.; Ponterini, G. (1994). "Generation of singlet oxygen by 2,2':5',2"-terthiophene and some of its derivatives". Journal of Photochemistry and Photobiology A. 83 (1): 1–6. doi:10.1016/1010-6030(94)03802-3. ISSN 1010-6030. CODEN: JPPCEJ.
  4. Perich, M. J.; Wells, C.; Bertsch, W.; Tredway, K. E. (1995). "Isolation of the insecticidal components of Tagetes minuta (Compositae) against mosquito larvae and adults". Journal of the American Mosquito Control Association. 11 (3): 307–310. PMID 8551298.
  5. Liu, Y.; Ye, M.; Guo, H. Z.; Zhao, Y. Y.; Guo, D. A. (2002). "New thiophenes from Echinops grijisii". Journal of Asian Natural Products Research. 4 (3): 175–178. doi:10.1080/1028602021000000071. ISSN 1028-6020. PMID 12118504. S2CID 41384356. CODEN: JANRFI.
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