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Self-assembly of vesicles from the stacking of a dipodal F?H-N hydrogen bonded arylamide foldamer
Authors:Lu Wang  Jun-Li Hou  Xi-Kui Jiang
Affiliation:a State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
b Department of Chemistry, Fudan University, Shanghai 200433, China
Abstract:In this paper, we report the synthesis and self-assembling behavior of an F?H-N hydrogen bonding-induced arylamide-based dipodal foldamer. SEM, AFM, TEM, and XRD studies reveal that this preorganized oligomer stacks to form vesicles in methanol-chloroform (10-70%) binary solvents due to the strong stacking interaction of the folded segments and the supramolecular polymeric feature of the dipodal molecule in the stacked state. In contrast, a simple folded molecule can give rise to vesicles only when the chloroform content is 45-55%.
Keywords:Foldamer   Vesicles   Hydrogen bonding   Self-assembly   Stacking   Aromatic amides
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