A self-assembled foldamer capsule: combining single and double helical segments in one aromatic amide sequence.
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.
Bao
Chunyan
C
Institut Européen de Chimie et Biologie, Université de Bordeaux-CNRS UMR5248 and UMS 3033, 2 rue Robert Escarpit, 33607 Pessac, France.
Gan
Quan
Q
Kauffmann
Brice
B
Jiang
Hua
H
Huc
Ivan
I
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
D000577:Amides