Shape-persistent macrocyclic aromatic tetrasulfonamides: Molecules with nanosized cavities and their nanotubular
1Colleges of Chemistry and Resources Science and Technology, Beijing Normal University, Beijing 100875, China. helan1961@hotmail.com
Summary
Alkoxy side-chain-flanked diarylsulfonamide enables the one-step synthesis of cone-shaped tetrasulfonamide macrocycles. These porous macrocycles self-assemble into tubular structures, offering potential for host-guest chemistry and nanoporous materials.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
Background:
- Diarylsulfonamide motifs are key for macrocycle construction.
- A specific 90-degree structural motif is known to be persistent in solution and solid states.
Purpose of the Study:
- To develop a reliable method for synthesizing macrocyclic aromatic tetrasulfonamides.
- To investigate the structural and conformational properties of these macrocycles.
- To explore their potential applications in host-guest chemistry and materials science.
Main Methods:
- Utilizing alkoxy side-chain-flanked diarylsulfonamide as a structural motif.
- One-step macrocyclization reaction.
- Solution and solid-state characterization (e.g., 1H NMR).
Main Results:
- Successful one-step formation of tetrasulfonamide macrocycles with a persistent 90-degree motif.
- Macrocycles adopt a stable cone-shaped conformation in solution and solid state, forming tunable internal cavities.
- Alkoxy side chains are crucial for maintaining the cone conformation.
- In solution, rapid interconversion of conformations is observed at room temperature.
- In the solid state, these molecules self-assemble into hollow tubular structures.
Conclusions:
- Alkoxy side-chain-flanked diarylsulfonamide is an effective building block for macrocyclic tetrasulfonamides.
- The resulting macrocycles exhibit tunable cavities and self-assembly properties.
- These molecules show promise as host molecules and building blocks for nanoporous materials.
