Terthiophene

From Wikipedia, the free encyclopedia
Terthiophene
IUPAC name

2,2':5',2"-terthiophene

Other names

α-Terthienyl
2,5-Di(2-thienyl)thiophene

Identifiers
CAS number 1081-34-1 N
PubChem 65067
ChemSpider 58578 YesY
ChEBI CHEBI:10335 YesY
ChEMBL CHEMBL90017 YesY
RTECS number WZ9717750
Jmol-3D images Image 1
Properties
Molecular formula C12H8S3
Molar mass 248.39 g/mol
Appearance pale yellow solid
Melting point 93-95 °C
Solubility in water insoluble
Hazards
S-phrases S22 S24/25
Main hazards flammable
Related compounds
Related compounds Thiophene
polythiophene
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.[1]

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.[2] It is responsible for the insecticidal activity of Tagetes minuta.[3]

Various substituted terthiophenes occur naturally, including 5,5''-dichloro-α-terthiophene, 5-chloro-α-terthiophene, 5-acetyl α-terthiophene, and 5-carboxyl bithiophene.[4]

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. (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. 
  2. ↑ 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. 
  3. ↑ 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. 
  4. ↑ 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. CODEN: JANRFI. 
This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.