Shoji Taku, Iida Nanami, Yamazaki Akari, Ariga Yukino, Ohta Akira, Sekiguchi Ryuta, Nagahata Tatsuki, Nagasawa Takuya, Ito Shunji
Graduate School of Science and Technology, Shinshu University, Matsumoto, 390-8621, Nagano, Japan.
Graduate School of Science and Technology, Hirosaki University, Hirosaki 036-8561, Aomori, Japan.
Org Biomol Chem. 2020 Mar 25;18(12):2274-2282. doi: 10.1039/d0ob00164c.
The preparation of phthalimides cross-conjugated with an azulene ring was established by a one-pot Diels-Alder reaction of the corresponding 2-aminofuran derivatives with several maleimides, without the isolation of the intermediately formed [4 + 2] cycloadducts. The structure, optical and electrochemical properties of the novel phthalimide derivatives were clarified by single-crystal X-ray analysis, UV/Vis and fluorescence spectra, spectroelectrochemistry and voltammetry experiments, and theoretical calculations. These results indicated that the substituents on the azulene ring greatly affect the optical and electrochemical properties of the molecules.
通过相应的2-氨基呋喃衍生物与几种马来酰亚胺的一锅法狄尔斯-阿尔德反应，实现了与薁环交叉共轭的邻苯二甲酰亚胺的制备，无需分离中间形成的[4 + 2]环加成物。通过单晶X射线分析、紫外/可见光谱和荧光光谱、光谱电化学和伏安法实验以及理论计算，阐明了新型邻苯二甲酰亚胺衍生物的结构、光学和电化学性质。这些结果表明，薁环上的取代基对分子的光学和电化学性质有很大影响。
