Reversible encapsulation of disc-shaped guests by a synthetic, self-assembled host

Academic Article
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publication date

  • 1996

abstract

  • Here, the synthesis of a bowl-shaped molecule is described and evidence of its reversible dimerization by means of hydrogen bonds is presented. The dimer features a flattened spherical cavity of peculiar symmetry and acts as a host for the encapsulation of guest molecules of complementary shape. Encapsulation of aromatic guests in chloroform solution and of cyclohexane in p-xylene solution was demonstrated by nuclear magnetic resonance experiments. The passage of guests into and out of the cavity is slow and occurs on a time scale of hours. The system was used to explore the effects of size, shape, and solvation on molecular recognition coupled with assembly.