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酰胺氢键相互作用对具有聚集诱导发光特性的萘二酰亚胺两亲分子超分子自组装的影响

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

作者信息

Ghule Namdev V, La Duong Duc, Bhosale Rajesh S, Al Kobaisi Mohammad, Raynor Aaron M, Bhosale Sheshanath V, Bhosale Sidhanath V

机构信息

Polymers and Functional Materials Division CSIR-Indian Institute of Chemical Technology Hyderabad Telangana 500 007 India.

School of Applied Sciences RMIT University GPO Box 2476 Melbourne VIC 3001 Australia.

出版信息

ChemistryOpen. 2016 Jan 11;5(2):157-63. doi: 10.1002/open.201500201. eCollection 2016 Apr.

DOI:10.1002/open.201500201
PMID:27308233
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4906475/
Abstract

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.

摘要

在本工作中,成功合成了两种新型萘二亚胺(NDI)两亲物NDI-N和NDI-NA,并对其自组装和光学性质进行了研究。对于含有酰胺基团的NDI-NA,在氯仿中存在不同比例的甲基环己烷(MCH)时表现出聚集诱导发光增强(AIEE),这导致了视觉颜色变化。这种新型含酰胺的NDI-NA两亲物在氯仿/MCH(10:90,v/v)中形成纳米带结构,在氯仿/MCH(5:95,v/v)中形成微杯状形态。这些微杯的封闭导致了囊泡和微胶囊的形成。通过红外光谱、X射线衍射以及扫描和透射电子显微镜等多种互补技术证实了通过NDI-NA的疏溶剂控制获得的结构形态。在NDI-N中不存在酰胺部分时,未观察到自组装现象,这表明氢键在自缔合过程中的重要作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c38f/4906475/2648758f7aa4/OPEN-5-157-g008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c38f/4906475/2648758f7aa4/OPEN-5-157-g008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c38f/4906475/45b41987b259/OPEN-5-157-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c38f/4906475/facb30516d08/OPEN-5-157-g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c38f/4906475/1d59fd67b929/OPEN-5-157-g006.jpg
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