A Self-Assembled Foldamer Capsule: Combining Single and Double Helical Segments in One Aromatic Amide Sequence

作者：Bao Chunyan; Gan Quan; Kauffmann Brice; Jiang Hua^*; Huc Ivan

来源：Chemistry - A European Journal, 2009, 15(43): 11530-11536.

DOI：10.1002/chem.200900877

• chirality
• helical structures
• molecular recognition
• supramolecular chemistry
• X-ray diffraction

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.

• 出版日期2009
• 单位中国科学院