Configurational and Constitutional Information Storage: Multiple Dynamics in Systems Based on Pyridyl and Acyl Hydrazones

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Abstract
The CN group of hydrazones can undergo E/Z isomerization both photochemically and thermally, allowing the generation of a closed process that can be tuned by either of these two physical stimuli. On the other hand, hydrazine‐exchange reactions enable a constitutional change in a given hydrazone. The two classes of processes: 1) configurational (physically stimulated) and 2) constitutional (chemically stimulated) give access to short‐term and long‐term information storage, respectively. Such transformations are reported herein for two hydrazones (bis‐pyridyl hydrazone and 2‐pyridinecarboxaldehyde phenylhydrazone) that undergo a closed, chemically or physically driven process, and, in addition, can be locked or unlocked at will by metal‐ion coordination or removal. These features also extend to acyl hydrazones derived from 2‐pyridinecarboxaldehyde. Similarly to the terpydine‐like hydrazones, such acyl hydrazones can undergo both constitutional and configurational changes, as well as metal‐ion coordination. All these types of hydrazones represent dynamic systems capable of acting as multiple state molecular devices, in which the presence of coordination sites furthermore allows the metal ion‐controlled locking and unlocking of the interconversion of the different states.

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