Thieno[3,4-c]pyrrole-incorporated quinoidal terthiophene with dicyanomethylene termini: Synthesis, characterization, and redox properties

Kyoko Takeda, Masafumi Shimawaki, Akiko Nakao, Itaru Osaka, Eigo Miyazaki, Kazuo Takimiya

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Synthesis, characterization, molecular structure, and redox properties of a new quinoidal terthiophene incorporated with a thieno[3,4-c]pyrrole moiety (5) are described. Although an electrochemical reduction of 5 formally produces the non-classical thieno[3,4-c]pyrrole moiety, 5 showed a reversible reduction wave on cyclic voltammogram, indicating that the thieno[3,4-c]pyrrole moiety can be stabilized by delocalized 10π-conjugated system in the dianion state of 5. However, the reduction potential was largely affected by incorporation of the thieno[3,4-c]pyrrole and shifted cathodically by 0.4 V compared to that of the parent quinodial terthiophene (1).

Original languageEnglish
Pages (from-to)4375-4377
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number33
DOIs
Publication statusPublished - 2010 Aug 18
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Thieno[3,4-c]pyrrole-incorporated quinoidal terthiophene with dicyanomethylene termini: Synthesis, characterization, and redox properties'. Together they form a unique fingerprint.

Cite this