Department of Chemistry, Faculty School of Science, Shinshu University, Matsumoto 390-8621, Japan.
Org Biomol Chem. 2012 Mar 28;10(12):2431-8. doi: 10.1039/c2ob06931h. Epub 2012 Feb 13.
Arylethynyl-2H-cyclohepta[b]furan-2-ones reacted with 7,7,8,8-tetracyanoquinodimethane (TCNQ) in a formal [2 + 2] cycloaddition reaction, followed by ring opening of the initially formed cyclobutene derivatives, to afford the corresponding dicyanoquinodimethane (DCNQ) chromophores in excellent yields. The intramolecular charge-transfer (ICT) interactions between the 2H-cyclohepta[b]furan-2-one ring and DCNQ acceptor moiety were investigated by UV/Vis spectroscopy and theoretical calculations. The redox behavior of the novel DCNQ derivatives was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties depended on the number of DCNQ units in the molecule. Moreover, a significant color change was observed by visible spectroscopy under electrochemical reduction conditions.
芳基乙炔基-2H-环庚[b]呋喃-2-酮与 7,7,8,8-四氰基对醌二甲烷（TCNQ）发生[2+2]环加成反应，随后开环形成的环丁烯衍生物，以优异的收率得到相应的二氰基醌二甲烷（DCNQ）生色团。通过紫外/可见光谱和理论计算研究了 2H-环庚[b]呋喃-2-酮环和 DCNQ 受体部分之间的分子内电荷转移（ICT）相互作用。通过循环伏安法（CV）和差分脉冲伏安法（DPV）研究了新型 DCNQ 衍生物的氧化还原行为，结果表明其多步电化学还原性质取决于分子中 DCNQ 单元的数量。此外，在电化学还原条件下通过可见光谱观察到明显的颜色变化。
