Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 43, Pages 11530-11536Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900877
Keywords
chirality; helical structures; molecular recognition; supramolecular chemistry; X-ray diffraction
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Funding
- French ANR [NT05-344880]
- Chinese Academy of Sciences
- National Natural Science Foundation of China [20772127]
- National Basic Research 973 Program of China [2009CB930802]
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In this manuscript, we present supramolecular capsules based on a new design relying on both self-assembly and folding of oligomeric strands. We have designed an aromatic amide foldamer in which each monomer encodes three levels of information: a specific cavity size, recognition groups for guest binding, and a propensity to adopt a single or a double helical motif. Thus, a tetradecameric sequence based on four different monomers was encoded so that a wide double helical segment resulting from the hybridization of two strands creates a cavity in which guests, such as 1,10-decanediol, can be bound. Additionally two narrow single helical segments form end-caps and isolate the guest from the solvent. The design, synthesis, solid-state and solution-state characterization of duplex formation and guest binding are presented.
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