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A Tubular Belt and a Möbius Strip with Dynamic Joints: Synthesis, Structure, and Host-Guest Chemistry
Jun Yuan1, Yunyi Song1, Xia Li1
1School of Chemistry, Sun Yat-Sen University, Guangzhou, Guangdong 510275, China.
Organic Letters
|December 6, 2021
Summary
Researchers synthesized two novel macrocycles, a tubular belt and a Möbius strip, using thianthrene. The tubular belt binds electron-deficient guests, while the Möbius strip shows ion-regulated dynamics, advancing macrocyclic chemistry.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Materials Science
Background:
- Macrocyclic chemistry is crucial for developing new materials and host-guest systems.
- Isomeric macrocycles offer unique structural and functional properties.
- Thianthrene-based macrocycles present opportunities for novel molecular architectures.
Purpose of the Study:
- To synthesize unprecedented isomeric macrocycles with thianthrene units.
- To investigate the host-guest properties of the tubular belt macrocycle.
- To explore the dynamic behavior of the Möbius strip macrocycle and its ion-regulation.
Main Methods:
- One-step cyclization reaction for macrocycle synthesis.
- Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy, mass spectrometry, and single-crystal X-ray diffraction.
- Complexation studies to determine host-guest interactions.
Main Results:
- Successful synthesis of two isomeric macrocycles: a tubular belt and a Möbius strip.
- Full structural characterization confirming the unprecedented nature of the isomers.
- Demonstration of the tubular belt's ability to encapsulate electron-deficient guests.
- Observation of twist-migration dynamics in the Möbius strip, tunable by sodium ions.
Conclusions:
- The facile synthesis of these unique thianthrene-based macrocycles expands the scope of belt chemistry.
- The tubular belt serves as a valuable host for specific guests.
- The Möbius strip's dynamic behavior offers potential for responsive molecular systems.
- These findings contribute to the understanding and application of complex macrocyclic structures.
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