{"title":"Chiral Self-Discrimination Induced Luminescence Vapochromism of Binaphthol Imides for Anti-Counterfeiting and Data Encryption","authors":"Yang Zhang, Hong-Ming Chen, Mei-Jin Lin","doi":"10.1002/adom.202400898","DOIUrl":null,"url":null,"abstract":"<p>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 <i>peri</i>-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.</p>","PeriodicalId":116,"journal":{"name":"Advanced Optical Materials","volume":null,"pages":null},"PeriodicalIF":8.0000,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Optical Materials","FirstCategoryId":"88","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/adom.202400898","RegionNum":2,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"MATERIALS SCIENCE, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
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.
期刊介绍:
Advanced Optical Materials, part of the esteemed Advanced portfolio, is a unique materials science journal concentrating on all facets of light-matter interactions. For over a decade, it has been the preferred optical materials journal for significant discoveries in photonics, plasmonics, metamaterials, and more. The Advanced portfolio from Wiley is a collection of globally respected, high-impact journals that disseminate the best science from established and emerging researchers, aiding them in fulfilling their mission and amplifying the reach of their scientific discoveries.