Dynamic Regulation of Supramolecular Chirality in an Amphiphilic Dimeric Macrocycle Through Azobenzene‐Based Photoisomerization
Source: PubMed Central Open Access, NCBI / U.S. National Library of Medicine
ABSTRACT The dynamic control of supramolecular chirality continues to represent a significant challenge in the development of adaptive functional materials. Inspired by dynamic planar chirality modulation and the host‐guest chemistry of pillararenes, we report a stimuli‐responsive supramolecular system capable of reversible chirality switching within an amphiphilic dimeric macrocycle (). This hybrid architecture, synthesized via‐functionalization of pillar[5]arene and [1]paracyclophane, preserves orthogonal host‐guest properties while exhibiting unique amphiphilicity‐directed self‐assembly behavior. Under UV irradiation,‐to‐isomerization of an alanine‐substituted azobenzene guest induces stereoselective binding modes, which dynamically modulate the planar chirality and morphologies of. Subsequent removal of the UV stimulus reverses the isomerization process, leading to the reformation of threaded complexes and the restoration of chiral supramolecular assemblies. This process demonstrates hierarchical regulation of supramolecular handedness via orthogonal molecular recognition pathways. The proposed strategy effectively integrates supramolecular chirality switching with stimuli‐responsive energy transduction, offering new avenues for the development of adaptive nanomaterials. A stimuli‐responsive supramolecular system has been rationally designed enabling hierarchical control over supramolecular handedness. This hybrid architecture retains orthogonal host‐guest properties and
Abstract
ABSTRACT The dynamic control of supramolecular chirality continues to represent a significant challenge in the development of adaptive functional materials. Inspired by dynamic planar chirality modulation and the host‐guest chemistry of pillararenes, we report a stimuli‐responsive supramolecular system capable of reversible chirality switching within an amphiphilic dimeric macrocycle (). This hybrid architecture, synthesized via‐functionalization of pillar[5]arene and [1]paracyclophane, preserves orthogonal host‐guest properties while exhibiting unique amphiphilicity‐directed self‐assembly behavior. Under UV irradiation,‐to‐isomerization of an alanine‐substituted azobenzene guest induces stereoselective binding modes, which dynamically modulate the planar chirality and morphologies of. Subsequent removal of the UV stimulus reverses the isomerization process, leading to the reformation of threaded complexes and the restoration of chiral supramolecular assemblies. This process demonstrates hierarchical regulation of supramolecular handedness via orthogonal molecular recognition pathways. The proposed strategy effectively integrates supramolecular chirality switching with stimuli‐responsive energy transduction, offering new avenues for the development of adaptive nanomaterials. A stimuli‐responsive supramolecular system has been rationally designed enabling hierarchical control over supramolecular handedness. This hybrid architecture retains orthogonal host‐guest properties and displays unique amphiphilicity‐directed chiral self‐assembly. advs75410-abs-0001 graphical