Issue 77, 2023

Chiroptical regulation of macrocyclic arenes with flipping-induced inversion of planar chirality

Abstract

Studies on various macrocyclic arenes have received increasing attention due to their straightforward syntheses, convenient derivatization, and unique complexation properties. Represented by pillar[n]arenes, several distinctive macrocyclic arenes have recently emerged with the following characteristics: they possess a pair of enantiomeric planar chiral conformations, and interconversion between these enantiomeric conformations can be achieved through the flipping of ring units. Complexation of a chiral guest with these macrocyclic arenes will lead to a shift of the equilibrium between the Rp and Sp conformers, leading to intriguing possibilities for chiral induction and sensing. By the introduction of bulky substituents on the rims, employing rotaxanation or pseudocatenation, planar chirality could be locked, enabling the enantiomeric separation of the chiral structures. The induced or separated chiral conformers/compounds exhibit significant chiroptical properties. These macrocyclic arenes, with flipping-induced inversion of planar chirality, demonstrated intriguing chiral induction dynamics and kinetics. In this featured review, we systematically summarize the progress in chiroptical induction/regulation of these macrocyclic arenes, particularly in the fields of chiral sensing, molecular machines, molecular recognition, and assembly.

Graphical abstract: Chiroptical regulation of macrocyclic arenes with flipping-induced inversion of planar chirality

Article information

Article type
Feature Article
Submitted
08 8 2023
Accepted
01 9 2023
First published
04 9 2023

Chem. Commun., 2023,59, 11469-11483

Chiroptical regulation of macrocyclic arenes with flipping-induced inversion of planar chirality

T. Zhao, W. Wu and C. Yang, Chem. Commun., 2023, 59, 11469 DOI: 10.1039/D3CC03829G

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