Effect of Amide Hydrogen Bonding Interaction on Supramolecular Self-Assembly of Naphthalene Diimide Amphiphiles with Aggregation Induced Emission.
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.
Polymers and Functional Materials Division CSIR-Indian Institute of Chemical Technology Hyderabad Telangana 500 007 India.
Namdev V
NV
Ghule
School of Applied Sciences RMIT University GPO Box 2476 Melbourne VIC 3001 Australia.
Duong Duc
DD
La
Polymers and Functional Materials Division CSIR-Indian Institute of Chemical Technology Hyderabad Telangana 500 007 India.
Rajesh S
RS
Bhosale
School of Applied Sciences RMIT University GPO Box 2476 Melbourne VIC 3001 Australia.
Mohammad
M
Al Kobaisi
School of Applied Sciences RMIT University GPO Box 2476 Melbourne VIC 3001 Australia.
Aaron M
AM
Raynor
School of Applied Sciences RMIT University GPO Box 2476 Melbourne VIC 3001 Australia.
Sheshanath V
SV
Bhosale
Polymers and Functional Materials Division CSIR-Indian Institute of Chemical Technology Hyderabad Telangana 500 007 India.
Sidhanath V
SV
Bhosale
aggregation-induced emission; amphiphile; cup-like morphology; nanostructures; naphthalene diimides; self-assembly