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Paper | Special issue | Vol 95, No. 1, 2017, pp.353-369
Published online, 11th November, 2016
DOI: 10.3987/COM-16-S(S)25
Synthesis and Electrochemical Properties of Azulene-Substituted Tetracyanobutadiene and Dicyanoquinodimethane Chromophores Connected with Naphthalene Cores

Taku Shoji,* Mitsuhisa Maruyama, Akifumi Maruyama, Daichi Nagai, Miwa Tanaka, Ryuta Sekiguchi, Shunji Ito, and Tetsuo Okujima

*Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan


Azulene-substituted tetracyanobutadienes (AzTCBDs) and dicyanoquinodimethanes (AzDCNQs) connected with naphthalene cores were prepared by the reaction of 1-azulenylalkynes with tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) in a formal [2 + 2] cycloaddition–retroelectrocyclization. The characteristic intramolecular charge transfer (ICT) characters were investigated by using UV/Vis spectroscopy and theoretical calculation. The redox behaviors of AzTCBDs and AzDCNQs were examined by cyclic voltammetry and differential pulse voltammetry, which revealed their properties of multi-electron transfer depending on the number of AzTCBD and AzDCNQ moieties. Moreover, significant color changes were observed by visible spectroscopy under the electrochemical reduction conditions.