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

Abstract

A novel C-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.

Fluorescence Regulation and Photoresponsivity in AIEE Supramolecular Gels Based on a Cyanostilbene Modified Benzene‐1,3,5‐Tricarboxamide Derivative

“…In addition, the first peak at 2.80° with a d ‐spacing of 3.15 nm in the small‐angle region was considered as the intermolecular distance in the orthogonal direction. In view of the columnar assemblies that most BTA structural molecules tended to form, and considering the fiber‐like microstructure of the gel (Figure a), the intermolecular distance might be attributed to the intercolumnar distance . Density functional theory calculations supported the conclusion that BTTPA molecules adopt a perfect equilateral triangle‐like structure with dimensions that were estimated to be 2.70 nm (Scheme S1).…”

A Three‐Armed Polymer with Tunable Self‐Assembly and Self‐Healing Properties Based on Benzene‐1,3,5‐tricarboxamide and Metal–Ligand Interactions

“…the fields ranging from organogels, [2][3][4][5] hydrogels, [6,7] nanostructured materials, [8] nucleating agents for polymers, [9] to microcapsules in biomedicine. [10] However, most of these researches mainly focused on the BTA-based small molecules [1,11,12] and there are limited reports about the synthesis and self-assembly of BTA-based polymers.…”

“…Benzene‐1,3,5‐tricarboxamide (BTA) is an important supramolecular building block, which can self‐assemble into 1D rod/fiber‐like structures by threefold H‐bonding . Because of this multivalent nature, BTA derivatives find wide applications in the fields ranging from organogels, hydrogels, nanostructured materials, nucleating agents for polymers, to microcapsules in biomedicine . However, most of these researches mainly focused on the BTA‐based small molecules and there are limited reports about the synthesis and self‐assembly of BTA‐based polymers.…”

A New Cationic Functionalized Pillar[5]arene and Applications for Adsorption of Anionic Dyes

“…), and find various potential applications. Furthermore, the easy modification of the two rims of pillar[5]arene made pillar[5]arene with extensive architectures and applications in topological chemistry, [31] bio-chemistry [32] and material science. [27] Pillar[5]arene consists of five 1,4-dimethoxy benzene subunits linked by methylene bridges cles in water and can potentially load negatively charged molecules such as congo red dye in water.…”