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Monosulfonated dibenzo-24-crown-8 and its properties.
M Woźny1, D Trzybiński2, K Dąbrowa1
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. mateusz.wozny@icho.edu.pl.
Organic & Biomolecular Chemistry
|June 22, 2022
Summary
We synthesized a new charged crown ether, monosulfonated dibenzo-24-crown-8 (SDB24C8), for advanced supramolecular chemistry. This SDB24C8 shows enhanced binding to cations, including an unusual preference for sodium.
Area of Science:
- Supramolecular Chemistry
- Macrocyclic Chemistry
- Crystallography
Background:
- Neutral dibenzo-24-crown-8 (DB24C8) ethers are known for cation binding.
- Developing permanently charged macrocycles is crucial for novel supramolecular applications.
- Functionalizing crown ethers can tune their host-guest properties.
Purpose of the Study:
- To develop a method for preparing a monosulfonated derivative of dibenzo-24-crown-8 ether (SDB24C8).
- To investigate the host-guest properties of the new anionic macrocycle, SDB24C8.
- To explore the potential of SDB24C8 in supramolecular chemistry.
Main Methods:
- Direct sulfonation of dibenzo-24-crown-8 (DB24C8) to yield SDB24C8.
- Crystallographic analysis of SDB24C8 complexed with hydronium and potassium cations.
- Supramolecular investigations and DFT calculations to study alkali cation interactions.
Main Results:
- Successful preparation of monosulfonated dibenzo-24-crown-8 (SDB24C8).
- First crystallographic data of a DB24C8-based host-guest complex involving hydronium and potassium.
- Increased binding affinities for alkali cations compared to the parent crown ether.
- Observed unusual selectivity of SDB24C8 towards sodium cations.
Conclusions:
- Monosulfonated dibenzo-24-crown-8 (SDB24C8) is a promising anionic macrocycle for supramolecular applications.
- The sulfonic acid group enhances cation binding affinities.
- SDB24C8 exhibits unique selectivity for sodium cations, warranting further investigation.
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