Terthiophene

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 Y
ChEBI CHEBI:10335 Y
ChEMBL CHEMBL90017 Y
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: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.

Contents

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, which is often lethal.[2] A variety of terthiophenes occur naturally, including 5,5''-dichloro-α-terthiophene, 5-chloro-α-terthiophene, 5-acetyl α-terthiophene, and 5-carboxyl bithiophene.[3]

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.