Chiral Self‐Discrimination Induced Luminescence Vapochromism of Binaphthol Imides for Anti‐Counterfeiting and Data Encryption.

Chiral self‐discrimination plays a critical role in supramolecular chemistry and materials science. However, an ideal strategy for achieving chiral self‐discrimination remains elusive due to the inevitable nonspecific binding of incorrect enantiomers, and insufficient intrinsic optical activity of chiral molecules. Herein, a novel 1,1′‐binaphthol (BINOL) derivative with an imide group fused at the peri‐position of one naphthol scaffold is developed, which combines the dual functionalities of aggregation‐induced emission characteristic of BINOLs, and high emission of 1,8‐naphthalimides. The multiple molecular recognition between two hydroxyl groups in BINOL units and two carbonyl groups in 1,8‐naphthalimide moieties endows the precise chiral self‐discrimination behaviors. As expected, the homochiral aggregates exhibit reversible phase transitions, switching from non‐emission to bright green emission upon absorption and desorption of methanol vapor. In contrast, the heterochiral conglomerates exhibit irreversible yellow emission changes due to the impact of chiral self‐discrimination. Such chiral self‐discrimination‐induced luminescence vapochromism can be further applied to high‐level anti‐counterfeiting and data encryption. This work provides a new perspective on smart chiral organic materials based on chiral self‐discrimination. [ABSTRACT FROM AUTHOR]