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Interplay between a Foldamer Helix and a Macrocycle in a Foldarotaxane Architecture
Maxime Gauthier1, Victor Koehler2, Caroline Clavel1
1Supramolecular Machines and ARchitectures Team, Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS, Université de Montpellier, ENSCM, case courrier 1706, Bâtiment Chimie (17), 3ème étage, Faculté des Sciences, Place Eugène Bataillon, 34095, Montpellier cedex 5, France.
Angewandte Chemie (International Ed. in English)
|January 21, 2021
Summary
Researchers developed a new rotaxane/foldaxane hybrid structure. A macrocycle acts as a shield, controlling how a helix binds to a dumbbell-shaped molecule, demonstrating tunable molecular recognition.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Materials Science
Background:
- Rotaxanes and foldaxanes are complex molecular architectures with potential applications in molecular machines and drug delivery.
- Understanding the interplay between different components in hybrid systems is crucial for designing advanced functional molecules.
- Oligoamide foldamers offer unique recognition properties due to their helical structures.
Purpose of the Study:
- To design and synthesize a novel hybrid architecture combining rotaxane and foldaxane features.
- To investigate the self-assembly process and recognition mechanisms within this hybrid system.
- To explore the role of a macrocycle as a modulator in molecular interactions.
Main Methods:
- Synthesis of a dumbbell-shaped guest molecule (axle) and a macrocycle.
- Construction of an aromatic oligoamide helix host.
- Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy and X-ray crystallography.
Main Results:
- Successful synthesis and characterization of the rotaxane/foldaxane hybrid architecture.
- Evidence of the oligoamide helix winding around the axle, influenced by the macrocycle's position.
- Demonstration that the macrocycle acts as a switchable shield, modulating helix-axle binding affinity.
- Observation of the foldamer helix compartmentalizing the axle and, in some cases, inducing macrocycle movement.
Conclusions:
- The study reports a novel hybrid molecular architecture with tunable recognition properties.
- The macrocycle's position and steric hindrance are key factors controlling molecular assembly.
- This work highlights the potential of using supramolecular auxiliaries to control molecular interactions in complex systems.
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