Electron-poor naphthalenediimides(NDIs) with large quadrupole moments and strong π-acidity have been extensively studied as ideal models to gain deep insights into anion-π interactions. The development of anion-NDI systems have attracted considerable attention with efforts on mechanisms and applications of the systems. Anion-to-NDI electron transfer induced by anion-π interactions in the system usually results in colorimetric change or the formation of characteristic spectra bands, which have become a convenient and efficient tactic for the design of anion sensors. Particularly, NDIs have shown distinct advantages in recognition of strong Lewis basic anions with the formation of easily identified UV bands corresponding to radical anions of NDIs. The paper surveys researches on anion-DNI interactions in recent years. The paper firstly presents the interactions and structures of anion-NDI systems, then extensively reviews the applications of anion-NDI interations in anion recognition, enantiomer recognition, organocatalysis, and construction of anion channel. The interactions of NDI with neutral molecules based on lone electron pair-π interactions are also included. The functional relevance of anion-π interactions is demonstrated upon the discussion of the developments and wide applications of anion-NDI systems. Finally, this paper summarizes the strategies and challenges in development of application-oriented anion-NDI systems and draws perspectives of anion-NDI interactions in fundamental studies and wide applications.
Contents
1 Introduction
2 Anion-NDI interactions
3 Applications of anion-NDI interactions in molecular recognition
3.1 Anion recognition and sensing
3.2 Recogntion of neutral molecules
3.3 pH responsiveness based on lone pair-NDI interactions
3.4 NDIs used for molecular electronics material
3.5 Enantiomer recognition
4 Applications of anion-NDI interactions in organocatalysis
5 Construction of anion channel with anion-NDI system
6 Conclusion and outlook