Supramolecular gel from self-assembly of a C<sub>3</sub>-symmetrical discotic molecular bearing pillar[5]arene.
basic_science · Level V
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- Record sourced from PubMed, PMID 28537314.
- Also identified by DOI 10.1039/c7sm00642j.
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Abstract
A novel C<sub>3</sub>-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.