Nature creates microenvironments to facilitate hydrogen bonding, e.g., bearing them inside DNA double helices or membrane ion channels. To design foldamers that mimics Nature’s way of using hydrogen bonds is a challenging task, mostly because of their conformational flexibility and large molecular size. Here, we utilize quantum mechanics to first design fragments and then compile them into functional sequences. Two examples are discussed. The first example takes advantages of the preorganization encoded into fragments to allow for anion-encapsulation. The second programs favourable electrostatic interactions to facilitate p-p stacking, leading to double helix formation. This work demonstrates ways to overcome obstacles commonly encountered in the nanometer scale, and thus opens up opportunities to facile design and quantitative understanding of complex supramolecular architectures.

Design foldamers from fragments: Chloride encapsulation and switchable double helices

251st National Meeting (2016)

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