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BowtieArene: A Dual Macrocycle Exhibiting Stimuli-Responsive Fluorescence
Sheng-Nan Lei1,2, Hongyan Xiao1,2, Yi Zeng1,2
1Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Key Laboratory of Bio-inspired Materials and Interfacial Science, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Angewandte Chemie (International Ed. in English)
|December 6, 2019
Summary
Researchers developed BowtieArene, a novel fluorescent molecule with unique cavities. This dual macrocycle displays switchable fluorescence triggered by various stimuli, offering new possibilities in supramolecular chemistry.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Chemistry
Background:
- Pillararenes are valuable in supramolecular chemistry but lack inherent fluorescence.
- Developing new macrocyclic compounds with integrated functionalities is an ongoing challenge.
Purpose of the Study:
- To introduce BowtieArene, a novel fluorescent dual macrocycle.
- To investigate its unique structural features, host-guest capabilities, and switchable fluorescence properties.
Main Methods:
- Concise synthesis of the figure-of-eight BowtieArene molecule.
- Experimental characterization of its vapor absorption and host-guest interactions.
- Investigation of fluorescence properties and stimuli-responsive behavior (solvent, vapor, mechanical force).
- Computational studies to understand the mechanism of fluorochromism.
Main Results:
- BowtieArene, a dual macrocycle with pillar-like cavities and a central fluorophore, was successfully synthesized.
- The molecule exhibits vapor absorption and host-guest capabilities.
- Intriguing switchable fluorescence was observed, triggered by solvent, vapor, and mechanical force.
- High reversibility and stability of the fluorescence switching were demonstrated.
Conclusions:
- BowtieArene represents a novel class of fluorescent macrocycles with potential applications in sensing and supramolecular chemistry.
- The observed fluorochromism is linked to molecular packing, providing insights into structure-property relationships.
- The stimuli-responsive nature of BowtieArene opens avenues for developing advanced functional materials.
