Light‐Gated Chirality in a Supramolecular Cavitand

Achieving precise and modulable chiral expression on molecular platforms is of great significance for the design and synthesis of chiroptical materials. Herein, we construct a supramolecular cavitand platform that enables programmable locking, switching, and rewriting of chiral information gated by light. A resorcin[4]arene‐based cavitand integrates multiple photoisomeriable stilbenes and alternating imidazole segments. By employing an outer‐wall binding strategy to bind multiple chiral carboxylic acids, it achieves efficient chirality transfer and enables the construction of a supramolecular chiral cavitand. Photoisomerization of embedded stilbene units, drives pathway‐dependent conformational transformations that govern chirality induction, retention, and erasure. Notably, different light channels (365/254 nm) enable distinct outcomes, including preservation of chiral host–guest complexes, disruption of propeller chirality, and complete guest release. Furthermore, chirality can be locked and retained in a propeller form after removing the chiral acids, demonstrating a light‐regulated chiral construction. The system further functions as a read‐write chiral information platform, allowing visualization, encryption, decryption, and erasure of chiroptical signals through programmable photochemical inputs. This work establishes a strategy for coupling photochemical control with supramolecular confinement, providing a proof‐of‐concept study of significant importance in chiral informatics.