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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Large N-Doped Zigzag Hydrocarbon Belts from Calixarenes: Synthesis, Structure, and Properties
Yi Peng1, Mei-Ling Tan1, Ke-Xing Ma1
1MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing, 100084, China.
Angewandte Chemie (International Ed. in English)
|May 26, 2025
Summary
Chemists synthesized large zigzag belts using calix[8]arenes, expanding molecular diversity beyond smaller resorcinarenes. These novel structures can host fullerenes, showing promise for advanced materials applications.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Materials Science
Background:
- Zigzag hydrocarbon belts and heteroatom-doped analogs possess unique structures and properties.
- Current synthetic methods, like the fjord-stitching approach, are limited in the size and diversity of achievable belts, primarily using resorcin[n]arenes (n=4, 6).
Purpose of the Study:
- To develop a method for synthesizing larger zigzag belts.
- To explore the structural and host-guest properties of these novel large belts.
Main Methods:
- Utilized conventional calix[8]arenes as starting materials.
- Employed multiple C─N cross-coupling reactions of per-brominated calix[8]arenes with anilines and ammonia.
- Incorporated selective transformation of 1,4-dihydroquinoline into quinolin-4(1H)-one segments.
Main Results:
- Successfully synthesized large zigzag belts with a unique octagonal prism cavity.
- Nitrogen atoms and functional groups are strategically positioned at the portals of the belts.
- The synthesized belts demonstrated high affinity for hosting fullerene guests (C60 and C70).
Conclusions:
- The developed synthetic strategy overcomes limitations of previous methods, enabling the creation of larger molecular belts.
- The unique structure facilitates strong host-guest interactions, driven by electronic and steric factors.
- These findings open new avenues for designing advanced host molecules for specific guest encapsulation.
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