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Supramolecular gel from self-assembly of a C3-symmetrical discotic molecular bearing pillar[5]arene

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Abstract

A novel C3-symmetric benzene-1,3,5-tricarboxamide (BTAs) decorated with three identical pillar[5]arene tails was designed, synthesized and characterized. The compound can gelate acetonitrile at low concentration (0.2 wt%) upon sonication at room temperature, but a precipitate was obtained by a conventional heating–cooling process. Scanning electron microscopy revealed that the gel and precipitate were constructed by entangled, high-aspect-ratio flexible bundles of nanofibrils. UV-vis spectroscopy, circular dichroism, Fourier transform infrared microscopy and powder X-ray diffraction showed that the compound formed chiral, elongated, columnar aggregates with nanofiber morphology by a combination of intermolecular hydrogen bonding between the N–H and C[double bond, length as m-dash]O of amides, π–π stacking (H-aggregates) and hydrophobic interactions of peripheral groups.

Graphical abstract: Supramolecular gel from self-assembly of a C3-symmetrical discotic molecular bearing pillar[5]arene

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Publication details

The article was received on 30 Mar 2017, accepted on 11 May 2017 and first published on 12 May 2017


Article type: Paper
DOI: 10.1039/C7SM00642J
Citation: Soft Matter, 2017, Advance Article
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    Supramolecular gel from self-assembly of a C3-symmetrical discotic molecular bearing pillar[5]arene

    X. Kuang, A. Wajahat, W. Gong, M. K. Dhinakaran, X. Li and G. Ning, Soft Matter, 2017, Advance Article , DOI: 10.1039/C7SM00642J

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