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Guest-induced, selective formation of isomeric capsules with imperfect walls

Academic Article
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Overview

authors

  • Jiang, W.
  • Rebek Jr., Julius

publication date

  • October 2012

journal

  • Journal of the American Chemical Society  Journal

abstract

  • 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.

subject areas

  • Dimerization
  • Ethers, Cyclic
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure
  • Resorcinols
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja3090737

PubMed ID

  • 23062190
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Additional Document Info

start page

  • 17498

end page

  • 17501

volume

  • 134

issue

  • 42

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