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Issue 4, 2020
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Aggregation-induced emission characteristics and solvent triggered hierarchical self-assembled chiral superstructures of naphthalenediimide amphiphiles

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Abstract

Herein, we report the design and synthesis of two naphthalene diimide amphiphiles NDI-TA1 and NDI-TA2 bearing acylated and deacylated hydroxyl groups of tartaric acid, respectively. Furthermore, we investigated the influence of acylation and deacylation of hydroxyl groups of tartaric acid over UV-vis, aggregation induced emission (AIE), chirality and supramolecular self-assembly formation. A bottom-up supramolecular self-assembly formation approach of the NDI-TA1 amphiphile exhibited biomimetic hairy caterpillar-like superstructures in a THF/MCH 30 : 70 v/v solvent system, whereas long uniform helical ribbons were also yielded at a higher volume percentage of MCH in THF (90 : 10 v/v). Circular dichroism (CD) spectroscopy studies revealed a chiral aspect of the self-assembled supramolecular structures at wavelengths corresponding to their absorptions. Interestingly, NDI-TA1 aggregates at higher amounts of MCH in THF exhibited AIE properties because of excimer formation. On the other hand, the NDI-TA2 amphiphile displays total quenching of emission, i.e. the aggregation cause quenching (ACQ) effect. The SEM images of deacylated amphiphile NDI-TA2 show belt and sheet-like supramolecular self-assembled microstructures.

Graphical abstract: Aggregation-induced emission characteristics and solvent triggered hierarchical self-assembled chiral superstructures of naphthalenediimide amphiphiles

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Supplementary files

Article information


Submitted
12 Oct 2019
Accepted
26 Dec 2019
First published
31 Dec 2019

New J. Chem., 2020,44, 1615-1623
Article type
Paper

Aggregation-induced emission characteristics and solvent triggered hierarchical self-assembled chiral superstructures of naphthalenediimide amphiphiles

D. A. Shejul, S. M. Wagalgave, R. W. Jadhav, M. A. Kobaisi, D. D. La, L. A. Jones, R. S. Bhosale, S. V. Bhosale and S. V. Bhosale, New J. Chem., 2020, 44, 1615
DOI: 10.1039/C9NJ05137F

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