Stable perylene diimide radical/alkylamine complex linked by asymmetric [CO⋯H⋯N]−1 -type strong H-bond and its color switching properties. (February 2023)

• Record Type: Journal Article
• Authors: Sun, Mengming; Liu, Hongliang; Yin, Gengwen; Hou, Wenlong; Liu, Lu; Liu, Xueqiang; Fan, Changzeng; Zhang, Haiquan
• Is Part Of: Dyes and pigments. Volume 209(2023)Supplement Part B
• Publication Date: 2023-02
• Subjects: Asymmetric anionic hydrogen bond -- Exchange of a hydrogen atom -- Hydrogen bond dynamics -- Perylene diimide radical anion -- pH-responsive color switching; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2022.110934
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Radical anions of electron-deficient systems are widely used, but they are easily reoxidized upon exposure to air. Therefore, the stabilization of radical anions under ambient conditions is of great significance, but still remains a scientific challenge. Here, perylene diimide radical anion species is stabilized by an asymmetric anionic low barrier strong hydrogen bond, which is reported firstly. The exchange of a hydrogen atom between one hydrogen atom in nitrogen atom of alkyl amine and the oxygen atom of the carbonyl on perylene diimide radical anion occurs to form such asymmetric anionic type strong hydrogen bond. This bond energy of hydrogen bond is evaluated by the apparent activation energy of thermal decomposition, and it is about 50 kcal/mol. The geometric states in this hydrogen bond depend on external conditions, including solvents and pH value, which will cause the change of their photophysical properties. The hydrogen bond complex shows excellent pH-responsive color switching performance based on the difference in geometric states of this hydrogen bond. Graphical abstract: To build stable perylene diimide radical anion species using an asymmetric anionic [CO⋯H⋯N] −1 -type strong H-bond. The geometric states of such anionic hydrogen bond depend on the surrounding environment, which then causes changes in their photophysical properties. It shows excellent pH-responsive color switching performance based on the change of surrounding environment. Image 1 Highlights: There are three highlights in our article. The three highlights are as follows: Air stable perylene diimide radical anion materials were constructed by using low barrier strong hydrogen bond [CO⋯H⋯N] −1 . The geometric structure of [CO⋯H⋯N] −1 depends on the environment and affects the photophysical properties. These perylene diimide radical anions can be used as new environmental responsive materials.