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Self-Assembly of Macrocyclic Hosts with Kinetic Inertness
Tayba Chudhary1, Yuxi Wei1, Lu Tong1
1Stoddart Institute of Molecular Science Department of Chemistry Zhejiang University, Hangzhou 310058, China.
Organic Letters
|October 20, 2025
Summary
Researchers synthesized macrocycles using dynamic covalent oxime condensation. Acid catalysis enables reversible oxime bonds, allowing for controlled synthesis and host-guest chemistry via hydrophobic interactions.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
Background:
- Dynamic covalent chemistry (DCC) offers adaptive molecular architectures.
- Oxime condensation is a versatile reaction for constructing complex molecules.
Purpose of the Study:
- To synthesize macrocycles utilizing oxime condensation.
- To investigate the role of acid catalysis in controlling the reaction.
- To explore the host-guest properties of the synthesized macrocycles.
Main Methods:
- Employed oxime condensation with strong acid catalysis.
- Utilized formyl precursors with varying water solubility.
- Investigated heterogeneous reaction conditions and catalyst addition rates.
- Assessed the kinetic inertness of macrocycles after catalyst removal.
- Examined guest accommodation via hydrophobic effects.
Main Results:
- Successfully synthesized macrocycles via acid-catalyzed oxime condensation.
- Demonstrated that slow acid addition prevents polymerization in heterogeneous reactions.
- Achieved kinetically inert macrocycles by removing the acid catalyst.
- Showcased macrocycle ability to bind guests through hydrophobic interactions.
Conclusions:
- Oxime condensation provides a controllable route to dynamic macrocycles.
- Acid catalysis is key to managing reactivity and achieving stable structures.
- Synthesized macrocycles exhibit potential for host-guest applications driven by hydrophobic forces.
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