Synthesis,Properties, and Redox Behavior of 1,1,4,4‐Tetracyano‐2‐ferrocenyl‐1,3‐butadienes Connected by Aryl,Biaryl, and Teraryl Spacers |
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| Authors: | Dr Taku Shoji Akifumi Maruyama Chisa Yaku Natsumi Kamata Prof Dr Shunji Ito Dr Tetsuo Okujima Prof Dr Kozo Toyota |
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| Institution: | 1. Department of Chemistry, Faculty School of Science, Shinshu University, Matsumoto 390‐8621, Nagano (Japan), Fax: (+)?81‐263‐37‐2476;2. Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto 390‐8621, Nagano (Japan);3. Graduate School of Science and Technology, Hirosaki University, Hirosaki 036‐8561, Aomori (Japan);4. Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama 790‐8577, Ehime (Japan);5. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980‐8578, Miyagi (Japan) |
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| 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. |
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| Keywords: | chromophores cycloaddition donor– acceptor systems ferrocene redox chemistry |
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