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A supramolecular host with a cavitand core and four cholate side arms
Beijun Cheng1, Marcos D García2, Yan Tian1
1School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan, 250353, China. bchengsd@163.com.
Organic & Biomolecular Chemistry
|February 24, 2026
Summary
A novel cavitand molecule was synthesized using copper-catalyzed azide-alkyne cycloaddition (CuAAC). This new molecule shows potential for binding viologen guests, with studies indicating a 1:1 complex formation.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Host-Guest Chemistry
Background:
- Cavitands are molecular hosts capable of encapsulating guest molecules.
- The synthesis of novel cavitand structures is crucial for advancing host-guest chemistry.
- Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is a reliable method for constructing complex molecular architectures.
Purpose of the Study:
- To synthesize a new cavitand functionalized with cholate groups.
- To investigate the host-guest complexation properties of the synthesized cavitand with viologen derivatives.
- To characterize the structure and binding behavior of the cavitand-guest complex.
Main Methods:
- Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) for synthesis.
- Spectroscopic techniques (NMR, MS) for characterization.
- Square wave voltammetry (SWV), Isothermal Titration Calorimetry (ITC), and Electrospray Ionization Mass Spectrometry (ESI-MS) for binding studies.
Main Results:
- A new cavitand (1) with four cholate groups was successfully synthesized and characterized.
- Complexation studies with 4,4'-bipyridinium (viologen) guests were performed in a H2O/DMSO mixture.
- Evidence for 1:1 stoichiometry complex formation between cavitand 1 and V2+ (viologen) was obtained via ITC and ESI-MS.
Conclusions:
- The synthesized cavitand demonstrates host-guest complexation capabilities with viologen derivatives.
- Computational studies suggest a compact globular structure and effective docking with methylviologen, but not inclusion complex formation.
- This work expands the library of functionalized cavitands for potential applications in molecular recognition.
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