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3453432 
Journal Article 
Effect of Amide Hydrogen Bonding Interaction on Supramolecular Self-Assembly of Naphthalene Diimide Amphiphiles with Aggregation Induced Emission 
Ghule, NV; La, DD; Bhosale, RS; Al Kobaisi, M; Raynor, AM; Bhosale, SV; Bhosale, SV 
2016 
5 
2 
157-163 
English 
27308233 
WOS:000374711500009 
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. 
cup-like morphology; self-assembly; aggregation-induced emission; nanostructures; naphthalene diimides; amphiphile