Open AccessEffect of Amide Hydrogen Bonding Interaction on Supramolecular Self‐Assembly of Naphthalene Diimide Amphiphiles with Aggregation Induced Emission
Author(s) -
Ghule Namdev V.,
La Duong Duc,
Bhosale Rajesh S.,
Al Kobaisi Mohammad,
Raynor Aaron M.,
Bhosale Sheshanath V.,
Bhosale Sidhanath V.
Publication year - 2016
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201500201
Subject(s) - chemistry , chloroform , self assembly , amphiphile , diimide , amide , hydrogen bond , supramolecular chemistry , perylene , photochemistry , crystallography , organic chemistry , molecule , polymer , crystal structure , copolymer
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.