SYNTHESIS AND PROPERTIES OF THIOPHENE AND DITHIIN FUNCTIONALIZED TETRATHIAFULVALENES


Ertas E., Bildirir H., Sahin O., Oksen I.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.188, no.12, pp.1835-1844, 2013 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 188 Issue: 12
  • Publication Date: 2013
  • Doi Number: 10.1080/10426507.2013.788005
  • Title of Journal : PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Page Numbers: pp.1835-1844

Abstract

Syntheses of two analogues of tetrathiafulvalene (TTF), fused to 1,4-dithiin and thiophene rings, substituted with thiophene moieties, have been illustrated. The syntheses were accomplished through the reaction of a 1,8-diketone with phosphorus pentasulfide or Lawesson's reagent in boiling dry toluene. Conversion of the thioketones to their the oxo forms with mercury (II) acetate, was followed by self-coupling in freshly distilled boiling triethyl phosphite. Attempts for their electro-polymerizations through the thiophene groups at the peripherals were unsuccessful. Computational chemistry studies revealed that the thiophene groups did not exhibit enough spin densities to perform polymerization. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.