A series of hydrogen-bonding motifs are shown to be capable of both high-fidelity and promiscuous molecular recognition behaviour. This gives rise to self-sorting and therefore well defined product distributions for up to four sequential phases of building block composition. Inclusion of a hydrogen-bonding motif that becomes capable of molecular recognition only upon photo-cleavage, extends the number of phases in the cascade to five. This supramolecular system thus reproduces multiple features of biological signalling cascades including the ability to switch between successive states comprising multiple well-defined complexes and triggered modification of molecular recognition preferences.
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