Guest-induced, selective formation of isomeric capsules with imperfect walls.
The majority of building blocks in self-assembled capsules feature high symmetry. Reducing this symmetry inevitably leads to expanded possibilities for isomerism. Here, we report a deep cavitand host with one short and three long walls. Its dimerization to hydrogen-bonded capsules in the presence of suitable guest molecules can lead to two constitutional isomers. A given guest induces the predominant formation of only one isomer. The unexpected selectivity is interpreted in terms of the different hydrogen-bonding patterns of the capsules and their effects on the size, shape, and dynamics of the capsules' spaces.
The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Wei
W
Jiang
Julius
J
Rebek
D019281:Dimerization; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D012118:Resorcinols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004988:Ethers, Cyclic; D012118:Resorcinols; C442939:cavitand