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Chiral softballs: synthesis and molecular recognition properties.
J M Rivera1, T Martín, J Rebek
1Contribution from The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Journal of the American Chemical Society
|July 18, 2001
Summary
Chiral softball dimers create dissymmetric cavities for enantioselective encapsulation of guests like terpenes. These flexible yet rigid capsules exhibit moderate selectivities and can interconvert between enantiomers.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Stereochemistry
Background:
- Softball structures are explored for their potential in molecular encapsulation.
- Understanding structural variants is key to achieving enantioselective properties.
Purpose of the Study:
- To investigate structural variants of softball congeners for enantioselective encapsulation.
- To design chiral capsules with dissymmetric cavities capable of differentiating enantiomers.
Main Methods:
- Synthesis of softball congeners with varying spacer elements.
- Characterization of dimeric softball structures and their cavity volumes.
- Complexation studies with asymmetric guests, including terpenes.
Main Results:
- Two distinct spacer elements induced chirality in the dimeric softball, despite achiral monomers.
- Dimeric softballs formed capsules with dissymmetric cavities (190–390 ų).
- Moderate enantioselectivities (up to 4:1) were observed for asymmetric guests, favoring one capsule enantiomer.
Conclusions:
- Chiral softball dimers effectively create dissymmetric cavities for enantioselective guest encapsulation.
- The host capsules exhibit a balance of flexibility and rigidity, enabling guest accommodation and stereochemical influence.
- Enantiomeric capsules demonstrate interconversion via dissociation and recombination, indicating dynamic behavior.
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