A current objective in supramolecular chemistry is to mimic the transitions between complex self‐sorted systems that represent a hallmark of regulatory function in nature. In this work, a self‐sorting network, comprising linear hydrogen motifs, was created. Selecting six hydrogen‐bonding motifs capable of both high‐fidelity and promiscuous molecular recognition gave rise to a complex self‐sorting system, which included motifs capable of both narcissistic and social self‐sorting. Examination of the interactions between individual components, experimentally and computationally, provided a rationale for the product distribution during each phase of a cascade. This reasoning holds through up to five sequential additions of six building blocks, resulting in the construction of a biomimetic network in which the presence or absence of different components provides multiple unique pathways to distinct self‐sorted configurations.

Hydrogen-bonding interactions are used to bias the conformation of an aromatic oligoamide foldamer in favour of an α-helix mimicking syn conformer.

A stimuli responsive linear hydrogen bonding motif, capable of in situ protonation and deprotonation, has been investigated. The interactions of the responsive hydrogen bonding motif with complementary partners were examined through a series of 1H NMR experiments, revealing that the recognition preference of the responsive hydrogen bonding motif in a mixture can be switched between two states.

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Miscible blends of poly(methyl methacrylate) and polystyrene polymers are assembled through triple hydrogen bonding between complementary ureidoimidazole and amidoisocytosine heterodimers.