Tuning Intramolecular Charge Transfer through Adjusting Hydrogen Bonding by Anions

Abstract

In this study we found that appropriate introduction of OH groups as the proton donor and amine as the electron donors to the perylene bisimide core can result in hydrogen‐bonded structures that facilitate tunable intramolecular charge transfer. Addition of F− anions can disrupt the intramolecular hydrogen bonds, therefore facilitate intracomplex proton transfer from O−H to F−, excess fluoride promotes deprotonation of the ground‐state complex. Therefore multiple fluorescence emission can be provided by this system. We used NMR, UV‐Vis‐NIR, and fluorescence spectroscopy to characterize these processes. The corresponding pronounced changes in photophysical properties (including color changes from green to blue to red) suggest new opportunities for creating novel functional supramolecular systems, such as multistate fluorescent switches.