Abstract
The construction of chemical sensors that can distinguish molecular chirality has attracted increasing attention in recent years due to the significance of chiral organic molecules and the importance of detecting their absolute configuration and chiroptical purity. The supramolecular chirality sensing strategy has shown promising potential due to its advantages of high throughput, sensitivity, and fast chirality detection. This review focuses on chirality sensors based on macrocyclic compounds. Macrocyclic chirality sensors usually have inherent complexing ability towards certain chiral guests, which combined with the signal output components, could offer many unique advantages/properties compared to traditional chiral sensors. Chirality sensing based on macrocyclic sensors has shown rapid progress in recent years. This review summarizes recent advances in chirality sensing based on both achiral and chiral macrocyclic compounds, especially newly emerged macrocyclic molecules.
Highlights
Chirality is a fundamental property of nature
Complexation of a chiral/achiral host molecule with a chiral guest molecule through non-covalent interactions including hydrogen bonds, van der Waals forces, π−π interaction, and electrostatic interactions will lead to new supramolecular enantiomers or diastereomers that could be discriminated by corresponding spectral analysis, including chiroptical techniques (e.g., circular dichroism (CD), vibrational circular dichroism (VCD), and circularly polarized luminescence (CPL))
We focus on the progress of research on supramolecular macrocyclic chiral sensors in the past decade
Summary
Chirality is a fundamental property of nature. Chiral molecules compose essential and fundamental components of living systems but could find wide applications in real life, such as in the pharmaceutical industry and materials science. Supramolecular chiroptical sensors provide a sensitive and fast-responding tool for determining the absolute configuration and enantiomeric excess (ee) of chemical compounds, which is promising for the use of real-time and high-throughput detection. Combined with the array analysis of multiple host molecules and data analysis, supramolecular chiroptical sensors could be highly promising for determining the absolute configuration and for differentiating compounds of different chemical structures [4,5,6]. The research on supramolecular chiroptical sensors can be roughly divided into two categories (Scheme 1): (1) Achiral macrocyclic sensors, which consist mainly of a chiral subunit, and their possible enantiomeric conformers that can rapidly interconvert. (2) Chiral macrocyclic sensors, which can form a diastereomeric complex with chiral guests In this case, a pair of enantiomers can be differentiated by the difference of the binding affinities between the host and the enantiomers. Sensing mechanisms for (a) achiral macrocyclic molecules and (b) chiral macrocyclic molecules
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