A Multistate Adaptive System of Topologically Distinct Chiral Assemblies.

Biological systems exemplify the extraordinary adaptability of living organisms to their surroundings, demonstrating the capacity to reconfigure their structure, properties, and function in response to specific environmental signals. In this context, the exploration of multistate chemical systems designed to mimic natural counterparts, with the capacity to precisely tailor the structural outcome of an assembly and perform a specific function in response to external triggers, remains largely unexplored. Herein, we present a multistate adaptive system of topologically distinct chiral assemblies obtained from a single amino acid-derived naphthalene diimide component and demonstrate its trigger-responsive properties. Our system yields five distinct supramolecular assemblies across both solution and solid states, achieved by modulation of external factors such as temperature, solvent, concentration, and guest molecules. The work demonstrates the remarkable adaptability of the non-covalent assemblies, revealing their profound sensitivity to external triggers, emphasizing the role of enthalpy and entropy in navigating across complex assembly pathways to and between individual outcomes.