Synthesis, properties, and redox behavior of 1,1,4,4-tetracyano-2-ferrocenyl-1,3-butadienes connected by aryl, biaryl, and teraryl spacers

Taku Shoji, Akifumi Maruyama, Chisa Yaku, Natsumi Kamata, Shunji Ito, Tetsuo Okujima, Kozo Toyota

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

Aryl-substituted 1,1,4,4-tetracyano-1,3-butadienes (FcTCBDs) and bis(1,1,4,4-tetracyanobutadiene)s (bis- FcTCBDs), possessing a ferrocenyl group on each terminal, were prepared by the reaction of a variety of alkynes with tetracyanoethylene (TCNE) in a [2+2] cycloaddition reaction, followed by retro-electrocyclization of the initially formed [2+2] cycloadducts (i.e., cyclobutene derivatives). The characteristic intramolecular charge transfer (ICT) between the donor (ferrocene) and acceptor (TCBD) moieties were investigated by using UV/Vis spectroscopy. The redox behaviors of FcTCBDs and bis-FcTCBDs were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their properties of multi-electron transfer depending on the number of ferrocene and TCBD moieties. Moreover, significant color changes were observed by visible spectroscopy under the electrochemical reduction conditions.

Original languageEnglish
Pages (from-to)402-409
Number of pages8
JournalChemistry - A European Journal
Volume21
Issue number1
DOIs
Publication statusPublished - 2015 Jan 2

Keywords

  • Chromophores
  • Cycloaddition
  • Donor-acceptor systems
  • Ferrocene
  • Redox chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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