AI Article Synopsis
- Molecular face-rotating polyhedra (FRP) are complex structures, and earlier attempts to create stereocontrolled FRP resulted in losing their inner space, which limits their usefulness in host-guest interactions.
- Through a rational design method, researchers successfully developed hollow FRP with high diastereoselectivity, allowing for better manipulation of their assembly.
- By understanding and adjusting the van der Waals repulsive forces between the building blocks, this study presents a new strategy for assembling pure organic cages, enhancing the potential applications of chiral materials.
Article Abstract
Molecular face-rotating polyhedra (FRP) exhibit complex stereochemistry, rendering it challenging to manipulate their assembly in a stereoselective manner. In our previous work, stereocontrolled FRP were gained at the cost of losing the confined inner space, which hampers their host-guest interactions and potential applications. Through a rational design approach, herein we demonstrate the successful construction of hollow FRP with high diastereoselectivity. Whereas the [4 + 4] imine condensation of -formyl substituted -symmetric and -symmetric led to the formation of all feasible FRP- diastereoisomers; the -substituted constitutional isomer, , exclusively assembled into a pair of homo-directional enantiomeric FRP--/ with a cavity size larger than 600 Å. Detailed structural characterizations and theoretical investigations revealed the thermodynamic landscape of FRP assembly can be effectively shaped by modulating the van der Waals repulsive forces among the facial building blocks. Our work provided a novel strategy towards stereospecific assembly of pure organic cages, opening up new opportunities for further applications of these chiral materials.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8442696 | PMC |
| http://dx.doi.org/10.1039/d1sc03428f | DOI Listing |
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