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Terthiophene

2,5-Di(2-thienyl)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

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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