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.