Synthesis of phthalimides cross-conjugated with an azulene ring, and their structural, optical and electrochemical properties
Taku Shoji, Nanami Iida, Akari Yamazaki, Yukino Ariga, Akira Ohta, Ryuta Sekiguchi, Tatsuki Nagahata, Takuya Nagasawa, Shunji Ito
Abstract
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.