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Clickable Bambusurils to Access Multivalent Architectures
Marine Lafosse1, Elise Cartier1, Kathleen Solmont1,2
1Université Paris-Saclay, CEA, Service de Chimie Bio-organique et de Marquage, 91191 Gif-sur-Yvette, France.
Organic Letters
|April 4, 2020
Summary
New propargylated bambusurils were synthesized and functionalized into multivalent architectures. These novel glycobambusurils exhibit good affinity for iodide anions in water.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Materials Science
Background:
- Bambusurils are macrocyclic compounds with potential applications in host-guest chemistry.
- Developing efficient synthetic routes for functionalized bambusurils is crucial for exploring their properties.
Purpose of the Study:
- To synthesize novel propargylated bambusurils.
- To create multivalent architectures through click chemistry.
- To develop water-soluble glycobambusuril platforms for potential anion sensing.
Main Methods:
- One-step condensation of dipropargylglycoluril with formaldehyde under microwave irradiation.
- Copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry for functionalization.
- Grafting of glycosides to impart water solubility.
Main Results:
- Efficient synthesis of propargylated bambus[4,6]urils.
- Successful creation of multivalent architectures with 8 or 12 ligands.
- Development of water-soluble glycobambusuril platforms.
- Glucosyl12BU[6] demonstrated good affinity for iodide anions in aqueous solution.
Conclusions:
- Propargylated bambusurils serve as versatile platforms for constructing complex molecular architectures.
- The developed glycobambusurils are water-soluble and show potential for anion recognition in aqueous environments.
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