Litcius/Paper detail

A Green and Wide‐Scope Approach for Chiroptical Sensing of Organic Molecules through Biomimetic Recognition in Water

Lili Wang, Mao Quan, Tilong Yang, Zhao Chen, Wei Jiang

2020Angewandte Chemie International Edition69 citationsDOI

Abstract

Optical chirality sensing has attracted a lot of interest due to its potential in high-throughput screening in chirality analysis. A molecular sensor is required to convert the chirality of analytes into optical signals. Although many molecular sensors have been reported, sensors with wide substrate scope remain to be developed. Herein, we report that the amide naphthotube-based chirality sensors have an unprecedented wide scope for chiroptical sensing of organic molecules. The substrates include, but are not limited to common organic products in asymmetric catalysis, chiral molecules with inert groups or remote functional groups from their chiral centers, natural products and their derivatives, and chiral drugs. The effective chirality sensing is based on biomimetic recognition in water and on effective chirality transfer through guest-induced formation of a chiral conformation of the sensors. Furthermore, the sensors can be used in real-time monitoring on reaction kinetics in water and in determining absolute configurations and ee values of the products in asymmetric catalysis.

Topics & Concepts

Chirality (physics)MoleculeNanotechnologySubstrate (aquarium)Molecular recognitionCombinatorial chemistryChemistryMaterials scienceChemical physicsOrganic chemistryPhysicsSymmetry breakingChiral symmetry breakingQuantum mechanicsOceanographyGeologyNambu–Jona-Lasinio modelMolecular spectroscopy and chiralityMolecular Sensors and Ion DetectionChemical Synthesis and Analysis