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Updated: Nov 16, 2025
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
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A shape-persistent arylene ethynylene macrocycle with a multiple acetamide modified cavity: synthesis and gelation.
Yang Ruan1, Qian-Hui Li, Lijin Shu
1Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, 310012, P. R. China. wan_junhua@hznu.edu.cn shulj@hznu.edu.cn.
Soft Matter
|February 24, 2021
Summary
A novel fluorescent macrocycle with amide groups was synthesized. This molecule selectively detects mercury ions and forms gels with unique nanoporous structures, exhibiting aggregation-induced enhanced emission.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Synthesis
Background:
- Arylene ethynylene macrocycles (AEMs) are versatile molecular platforms.
- Developing functional macrocycles with specific properties like fluorescence and gelation is an active research area.
- The incorporation of hydrogen-bonding motifs can influence macrocycle assembly and properties.
Purpose of the Study:
- To synthesize a novel arylene ethynylene macrocycle (AEM) bearing endo-acetamide groups.
- To investigate the self-assembly, fluorescence, metal ion sensing, and gelation properties of the new AEM.
- To explore the potential of AEMs in developing advanced functional materials.
Main Methods:
- Pd/Cu-mediated homo-coupling reaction for macrocycle synthesis.
- 1H NMR spectroscopy to study aggregation behavior in solution.
- Fluorescence spectroscopy for metal ion sensing studies.
- Solvent gelation experiments.
- Scanning Electron Microscopy (SEM) and Transmission Electron Microscopy (TEM) for morphological analysis.
Main Results:
- A new AEM with endo-acetamide groups was successfully synthesized with improved cyclization yield (30%) by incorporating a tetraethylene glycol ether linker.
- The macrocycle forms strong hydrogen-bonded aggregates in solution and exhibits fluorescence.
- It demonstrates highly selective fluorescence quenching in the presence of Hg2+ ions.
- The macrocycle induces gelation in various solvents and displays aggregation-induced enhanced emission (AIEE) upon gelation.
- SEM and TEM revealed nanoporous structures in the resulting xerogels.
Conclusions:
- A novel fluorescent AEM with amide groups was designed and synthesized.
- The macrocycle shows potential as a selective Hg2+ sensor and a gelator.
- The observed AIEE behavior and nanoporous structures highlight its utility in materials science.
- This study presents a new molecular design strategy for fluorescent gels from planar AEMs.
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