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Synthesis, Properties, and Redox Behavior of 1,1,4,4‐Tetracyano‐2‐ferrocenyl‐1,3‐butadienes Connected by Aryl, Biaryl, and Teraryl Spacers
Author(s) -
Shoji Taku,
Maruyama Akifumi,
Yaku Chisa,
Kamata Natsumi,
Ito Shunji,
Okujima Tetsuo,
Toyota Kozo
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405004
Subject(s) - ferrocene , tetracyanoethylene , cyclic voltammetry , chemistry , redox , intramolecular force , differential pulse voltammetry , aryl , photochemistry , cycloaddition , acceptor , medicinal chemistry , electron transfer , electrochemistry , stereochemistry , organic chemistry , catalysis , alkyl , physics , electrode , condensed matter physics
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.