Synthesis and electronic properties of 4- cyanophenylvinylenedithiathiophene: An EDOT derivative

Oznur Sucsoran, Somer Bekiroglu, Turan Ozturk, Erdal Ertas*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Synthesis of 4-cyanophenylvinylenedithiathiophene, which is an analogue of ethylenedioxythiophene (EDOT), has been described. The synthesis was achieved by applying 1,8-diketone ring formation reaction occurring between 1,8-diketone and phosphorus decasulfide in boiling toluene. The target compound was characterized by cyclic voltammetry (CV), UV spectroscopy, and theoretical studies. Unlike the analogues similarly carrying phenyl groups substituted with other functional groups such as -OMe, -Br, -NO 2, neither electrochemical polymerization attempts nor chemical polymerization efforts with ferric chloride(III) (FeCl 3) succeeded in yielding any products. Results of spin density calculations revealed that the molecule did not have enough electron spin densities at the "α" carbons of the thiophene part. Moreover, during the polymerization attempt with FeCl 3, as the nitrile nitrogen could form complex with iron, spin density calculation was also performed for protonated form of the monomer, which indicated that the "α" carbons of the molecule had even lower spin densities.

Original languageEnglish
Pages (from-to)49-53
Number of pages5
JournalSynthetic Metals
Volume162
Issue number1-2
DOIs
Publication statusPublished - Feb 2012

Keywords

  • 4-Cyanophenylvinylenedithiathiophene
  • Ethylenedioxythiophene
  • Phosphorus decasulfide (P S )
  • Radical spin density dithiin

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