Synthesis and Study of the Anodic Behavior of 1,3,4,6-Tetraaryl-2λ 4 δ 2 -thieno[3,4-c]thiophenes

Abstract

Two heterocyclic compounds based on the thieno[3,4-c]thiophene structure with four aryl substituents were prepared and their behavior in electrooxidation studied. These tetraarylthieno[3,4-c]thiophenes were synthesized in three steps starting from 1,3-dibenzoylmethane in the case of 1,3,4,6-tetraphenyl-2 u 4 i 2 -thieno[3,4-c]thiophene 1a and from 1,3-bis(4'-methoxyphenyl)propane-1,3-dione in the case of 1,3,4,6-tetrakis(4'-methoxyphenyl)-2 u 4 i 2 -thieno[3,4-c]thiophene 1b , a new compound. Both cyclic and hydrodynamic voltamperometric analyses indicate two reversible one-electron oxidation stages for compound 1b , while for compound 1a only the first stage is reversible. The preparative electrooxidation of the two compounds results in the opening of one thiophene ring giving rise to n -keto-thioketones.

Keywords:

• Cation Radical
• Electrooxidation
• Thieno[3,4-c]thiophene
• Thioketone
• Thiophene