Real-Time Direct Monitoring of Chirality Fixation and Recognition at the Single-Molecule Level

• Published in: Journal of the American Chemical Society Vol. 146; no. 26; pp. 17765 - 17772
• Main Authors: Hu, Weilin, Li, Mingyao, Xiong, Wan, Zhou, Shuyao, Zou, Qi, Lü, Jing-Tao, Tian, He, Guo, Xuefeng
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 03.07.2024
• Subjects: optical isomerism; pharmacology; structure-activity relationships; synergism
• DOI: 10.1021/jacs.4c03071
• ISSN: 0002-7863; 1520-5126

Chirality, a fundamental attribute of nature, significantly influences a wide range of phenomena related to physical properties, chemical reactions, biological pharmacology, and so on. As a pivotal aspect of chirality research, chirality recognition contributes to the synthesis of complex chiral products from simple chiral compounds and exhibits intricate interplay between chiral materials. However, macroscopic detection technologies cannot unveil the dynamic process and intrinsic mechanisms of single-molecule chirality recognition. Herein, we present a single-molecule detection platform based on graphene-molecule-graphene single-molecule junctions to measure the chirality recognition involving interactions between amines and chiral alcohols. This approach leads to the realization of in situ and real-time direct observation of chirality recognition at the single-molecule level, demonstrating that chiral alcohols exhibit compelling potential to induce the formation of the corresponding chiral configuration of molecules. The amalgamation of theoretical analyses with experimental findings reveals a synergistic action between electrostatic interactions and steric hindrance effects in the chirality recognition process, thus substantiating the microscopic mechanism governing the chiral structure–activity relationship. These studies open up a pathway for exploring novel chiral phenomena from the fundamental limits of chemistry, such as chiral origin and chiral amplification, and offer important insights into the precise synthesis of chiral materials.