Thermally Sensitive Self-Assembly of Glucose-Functionalized Tetrachloro-Perylene Bisimides: From Twisted Ribbons to Microplates

Chiral supramolecular structures are becoming increasingly attractive for their specific molecular arrangements, exceptional properties, and promising applications in chiral sensing and separation. However, constructing responsive chiral supramolecular structures remains a great challenge. Here, glucose-functionalized tetrachloro-perylene bisimides (GTPBIs) with thermally sensitive self-assembly behaviors are designed and synthesized. In a methanol/water mixture, GTPBIs self-assembled into twisted ribbons and microplates at 4 and 25 °C, respectively. Furthermore, the ribbon structure was metastable and could transform into microplates when the temperature was increased from 4 to 25 °C. Transmission electron microscopy (TEM) was used to track the evolution of morphology and study the assembly mechanisms of correponding nanostructures at different time intervals. The supramolecular structures were characterized with various techniques, including circular dichroism, TEM, scanning electron microscopy, atomic force microscopy, ultraviolet-visible absorption, and fluorescence spectra. This study provides insight into controlling molecular parameters and assembly conditions to construct chiral supramolecular structures.