Nano‐sized toroids and lemniscates assembled from self‐organization of a <i>C</i><scp><sub>3</sub></scp>‐symmetry organogelator

Abstract A novel C ₃‐symmetric organogelator based on a tris(triazolylmethyl)benzene core functionalized with three long‐chain pyridine‐2,6‐dicarboxamide branches has been successfully synthesized using a straightforward and modular “click chemistry” approach. This design enables efficient molecular construction while allowing for precise control over supramolecular functionality. The resulting molecule exhibits robust self‐assembly behavior, driven by a synergistic interplay of noncovalent interactions, including intermolecular hydrogen bonding, π–π stacking between aromatic moieties, and van der Waals forces among the flexible alkoxyl chains. Upon self‐organization in suitable solvents, the organogelator forms a three‐dimensional network that immobilizes the liquid phase, resulting in gelation. Advanced imaging techniques such as atomic force microscopy and fluorescence microscopy reveal the formation of intricate supramolecular nanostructures, including lemniscate (figure‐eight) and toroidal morphologies, underscoring the unique self‐assembly capabilities associated with the compound 1. These findings not only demonstrate the potential of triazole‐linked aromatic cores integrated with long‐chain pyridine‐2,6‐dicarboxamides as versatile scaffolds for supramolecular gelators but also highlight their promise for applications in nanomaterials, soft matter, and functional supramolecular architectures.

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Publication Details

Journal
Journal of the Chinese Chemical Society
Published
2025-08-20
DOI
https://doi.org/10.1002/jccs.70079
Primary Topic
Supramolecular Self-Assembly in Materials
Type
article
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article

Nano‐sized toroids and lemniscates assembled from self‐organization of a C3‐symmetry organogelator

Kai‐Chi Chang, Shih‐Sheng Sun, Mandy M. Lee, Ashutosh S. Singh et al.
Journal of the Chinese Chemical Society
Supramolecular Self-Assembly in Materials
article

Nano‐sized toroids and lemniscates assembled from self‐organization of a C3‐symmetry organogelator

Kai‐Chi Chang, Shih‐Sheng Sun, Mandy M. Lee, Ashutosh S. Singh, Sie‐Rong Li, Meng‐Shiue Tsai, Joseph Jen‐Tse Huang, Ruei‐Yu He
article en

Abstract

Abstract A novel C ₃‐symmetric organogelator based on a tris(triazolylmethyl)benzene core functionalized with three long‐chain pyridine‐2,6‐dicarboxamide branches has been successfully synthesized using a straightforward and modular “click chemistry” approach. This design enables efficient molecular construction while allowing for precise control over supramolecular functionality. The resulting molecule exhibits robust self‐assembly behavior, driven by a synergistic interplay of noncovalent interactions, including intermolecular hydrogen bonding, π–π stacking between aromatic moieties, and van der Waals forces among the flexible alkoxyl chains. Upon self‐organization in suitable solvents, the organogelator forms a three‐dimensional network that immobilizes the liquid phase, resulting in gelation. Advanced imaging techniques such as atomic force microscopy and fluorescence microscopy reveal the formation of intricate supramolecular nanostructures, including lemniscate (figure‐eight) and toroidal morphologies, underscoring the unique self‐assembly capabilities associated with the compound 1. These findings not only demonstrate the potential of triazole‐linked aromatic cores integrated with long‐chain pyridine‐2,6‐dicarboxamides as versatile scaffolds for supramolecular gelators but also highlight their promise for applications in nanomaterials, soft matter, and functional supramolecular architectures.

Journal of the Chinese Chemical SocietyVol. 72(10)
Maharishi Markandeshwar University, Mullana (IN), National Chi Nan University (TW), Institute of Chemistry, Academia Sinica (TW)
Openalex Percentile: Top 86%
Supramolecular Self-Assembly in Materials
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