Triazine- and Binaphthol-Based Chiral Macrocycles and Cages: Synthesis, Structure, and Solid-State Assembly.
Huan Zhang1,2, Yu-Fei Ao1,2, De-Xian Wang1,2
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
The Journal of Organic Chemistry
|February 16, 2022
Summary
Researchers synthesized chiral macrocycles and cages from triazine and binaphthol units. These enantiopure compounds exhibit unique chiral cavities and self-assembly properties, forming ordered structures with helical channels.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Crystallography
Background:
- Chiral macrocycles and cages are crucial in molecular recognition and catalysis.
- Developing efficient synthetic routes for enantiopure complex architectures remains a challenge.
Purpose of the Study:
- To develop facile synthetic methods for novel triazine- and binaphthol-based chiral macrocycles and cages.
- To investigate the self-assembly properties and structural characteristics of these new compounds.
Main Methods:
- Fragment coupling and one-pot synthesis strategies were employed.
- Multigram scale synthesis of enantiopure products was achieved.
- Crystal structure analysis was used to determine molecular architecture and assembly.
Main Results:
- A series of homochiral and heterochiral macrocycles and cages were synthesized in 52-91% yields.
- Crystal structures revealed intricate chiral cavities and unique assembly behaviors.
- (S,S,S)-Cage displayed a D3-symmetric propeller-like structure with chiral pockets.
Conclusions:
- The study presents efficient synthetic routes to enantiopure chiral macrocycles and cages.
- These compounds demonstrate promising self-assembly properties, forming ordered crystalline structures.
- The chiral cavities and structural features hold potential for applications in host-guest chemistry and asymmetric catalysis.
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