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Updated: Mar 19, 2026
09:44
Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
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Cone p-aminocalix[4]arenes enriched with 'clickable' alkyne or azide functionalities.
Ilia Korniltsev1, Vasily Bazhenov1, Alexander Gorbunov1
1Department of Chemistry, M. V. Lomonosov Moscow State University, Lenin's Hills 1, 119991 Moscow, Russia.
Beilstein Journal of Organic Chemistry
|March 18, 2026
Summary
New methods synthesize multifunctional calixarenes with amino and clickable groups. These platforms enable the creation of complex supramolecular assemblies and advanced macrocyclic structures.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Macrocyclic Chemistry
Background:
- Calixarenes are versatile macrocyclic hosts with tunable properties.
- Functionalization of calixarene rims is key to developing advanced materials.
- Click chemistry offers efficient methods for molecular assembly.
Purpose of the Study:
- To develop efficient synthetic routes for heteromultifunctional calix[4]arenes.
- To create calixarene platforms with both amino and clickable functionalities (alkyne or azide).
- To demonstrate the utility of these platforms in synthesizing complex supramolecular structures.
Main Methods:
- Synthesis of propargylated and 2-azidoethylated p-aminocalix[4]arenes using multi-step strategies.
- Protection of amino groups as tert-butoxycarbonyl (Boc) derivatives for purification and transformation.
- Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) 'click' reactions for triazole formation.
- Subsequent functionalization of amino groups to form tetraureacalix[4]arenes.
Main Results:
- Successfully synthesized five types of multifunctional calix[4]arenes with diverse functional groups.
- Demonstrated efficient 'click' reactions to form triazolated macrocycles.
- Obtained narrow-rim triazolated tetraureacalix[4]arenes, showing potential for capsule formation.
- Confirmed that triazole groups do not hinder the formation of supramolecular capsules.
Conclusions:
- The developed p-aminocalix[4]arenes serve as versatile platforms for further functionalization.
- These platforms facilitate the synthesis of sophisticated supramolecular assemblies with tailored properties.
- The combination of amine reactivity and click chemistry provides a powerful toolkit for macrocycle design.
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