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Terthiophene

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Terthiophene
Terthiophene
Terthiophene
Names
IUPAC name 2,2':5',2"-terthiophene
Other names α-Terthienyl
2,5-Di(2-thienyl)thiophene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.168.218 Edit this at Wikidata
PubChem CID
RTECS number
  • WZ9717750
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
Related compounds
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, which is often lethal. A variety of terthiophenes occur naturally, including 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. Smeets, B. J. J.; Meijer, R. H.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. "Process Design and Scale-Up of the Synthesis of 2,2':5',2-Terthienyl" Organic Process Research & Development (2003), volume 7, pages 10-16.
  2. Ciofalo, Maurizio; Ponterini, Glauco. Generation of singlet oxygen by 2,2':5',2"-terthiophene and some of its derivatives. Journal of Photochemistry and Photobiology, A: Chemistry (1994), 83(1), 1-6. CODEN: JPPCEJ ISSN:1010-6030.
  3. Liu, Y.; Ye, M.; Guo, H.-Z.; Zhao, Y.-Y.; Guo, D.-A. "New thiophenes from Echinops grijisii" Journal of Asian Natural Products Research (2002), volume 4, pages 175-178. JANRFI ISSN:1028-6020.
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