Effect of Amide Hydrogen Bonding Interaction on Supramolecular Self‐Assembly of Naphthalene Diimide Amphiphiles with Aggregation Induced Emission

摘要

In the present work, two new naphthalene diimide (NDI) amphiphiles, >NDI‐N and >NDI‐NA, were successfully synthesized and employed to investigate their self‐assembly and optical properties. For >NDI‐NA, which contains an amide group, aggregation‐induced emission enhancement (AIEE) was demonstrated in the presence of various ratios of methylcyclohexane (MCH) in chloroform, which led to the visual color changes. This new amide‐containing >NDI‐NA amphiphile formed nanobelt structures in chloroform/MCH (10:90, v/v) and microcup‐like morphologies in chloroform/MCH (5:95, v/v). The closure of these microcups led to the formation of vesicles and microcapsules. The structural morphologies gained from the solvophobic control of >NDI‐NA were confirmed by various complementary techniques such as infrared spectroscopy, X‐ray diffraction, and scanning and transmission electron microscopy. In the absence of the amide moiety in >NDI‐N, no self‐assembly was observed, indicating the fundamental role of H‐bonding in the self‐association process.