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Published on: April 1, 2013
Acridane[4]Arenes: Scope of the Macro-Tetramerization, Derivatization Options, and Water-Soluble Derivatives
Vera Höft1, Jonathan Pfeuffer-Rooschüz1, Ricard López-Coll1
1Department of Chemistry, University of Basel, Basel, Switzerland.
Acridane[4]arenes (A4A) are versatile macrocycles optimized for supramolecular chemistry. New functionalization strategies yield diverse derivatives, including self-assembling cages and water-soluble compounds for broad applications.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Macrocyclic Chemistry
Background:
- Macrocycles are crucial in supramolecular chemistry.
- Acridane[4]arenes (A4A) are a novel macrocyclic platform.
- A4A offers a conformationally restricted bowl shape.
Purpose of the Study:
- Optimize A4A synthesis and expand its scope.
- Develop derivatization strategies for A4A.
- Explore A4A's potential in supramolecular applications.
Main Methods:
- Expanded macrocyclization scope with varied lower rim substituents.
- Developed selective upper rim functionalization via N-Boc protection.
- Utilized Buchwald-Hartwig cross-coupling for N-functionalization.
Main Results:
- Achieved self-assembly into dimeric cages with N-Boc protected A4A.
- Demonstrated stable host-guest complex formation with tetrabutylammonium salts.
- Created water-soluble A4A derivatives using ionic lower rim substituents.
Conclusions:
- A4As are highly modular macrocyclic platforms.
- Established comprehensive derivatization strategies for A4A.
- A4A exhibits broad potential for supramolecular chemistry and applications.
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