Multiple adaptation of constitutional dynamic networks and information storage in constitutional distributions of acylhydrazones

We report a study of the behavior of four dynamic covalent libraries (DCLs) based on acylhydrazones (a)A(b)B and of the corresponding square constitutional dynamic networks (CDNs) NA–ND under the effect of three agents, namely, metal cations, base + metal cations and light irradiation; in particular, the successful switching of the CDN NB between two orthogonal distributions results, respectively, from metallo-selection and photo-selection. The four DCLs undergo triple adaptation when subjected to the three agents with the generation of specific CDN distributions characteristic of each of the four DCLs. The ternary outputs displayed by the DCLs present three states (–1, 0 and 1) related to three different constitutional distributions expressed in response to the triple inputs applied. This latter process amounts to the storage of molecular information in dynamic distributions rather than in selective interactions between complementary entities undergoing molecular recognition.