Alignment and Dynamic Inversion of Planar Chirality in Pillar[n]arenes
- 10 August 2023
- journal article
- review article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 62 (47) , e202308316
Abstract
Pillar[n]arenes are symmetrical macrocyclic compounds composed of benzene panels with para‐methylene linkages. Each panel usually exhibits planar chirality and prefers chirality‐aligned states. Because of this feature, pillar[n]arenes are attractive scaffolds for chiroptical materials that are easy to prepare and optically resolve and show intense circular dichroism (CD) signals. In addition, rotation of the panels endows the chirality of pillar[n]arenes with a dynamic nature. The chirality in tubular oligomers and supramolecular assemblies sometimes show time‐ and procedure‐dependent alignment phenomena. Furthermore, the CD signals of some pillar[n]arenes respond to the addition of chiral guests when their dynamic chirality is coupled with host–guest properties. By using diastereomeric pillar[n]arenes with additional chiral structures, the response can also be caused by achiral guests and changes of the environment, providing molecular sensors.Keywords
Funding Information
- Japan Society for the Promotion of Science (JP20K22528, JP21K14611, JP23H04027, JP19H00909, JP22H00334, JP22K19063)
- Core Research for Evolutional Science and Technology (JPMJCR18R3)
- National Natural Science Foundation of China (22271232)
This publication has 77 references indexed in Scilit:
- Achiral guest-induced chiroptical changes of a planar-chiral pillar[5]arene containing one π-conjugated unitChemical Communications, 2013
- Incorporation of an A1/A2-Difunctionalized Pillar[5]arene into a Metal–Organic FrameworkJournal of the American Chemical Society, 2012
- Pillararenes, A New Class of Macrocycles for Supramolecular ChemistryAccounts of Chemical Research, 2012
- Planar-Chiral Macrocyclic Host Pillar[5]arene: No Rotation of Units and Isolation of Enantiomers by Introducing Bulky SubstituentsOrganic Letters, 2011
- Planar-Chiral Pillar[5]arene: Chiral Switches Induced by Multiexternal Stimulus of Temperature, Solvents, and Addition of Achiral Guest MoleculeThe Journal of Organic Chemistry, 2010
- Synthesis and Conformational Characteristics of Alkyl-Substituted Pillar[5]arenesThe Journal of Organic Chemistry, 2010
- Effect of an Intramolecular Hydrogen Bond Belt and Complexation with the Guest on the Rotation Behavior of Phenolic Units in Pillar[5]arenesThe Journal of Physical Chemistry Letters, 2010
- Polymeric RotaxanesChemical Reviews, 2009
- para-Bridged Symmetrical Pillar[5]arenes: Their Lewis Acid Catalyzed Synthesis and Host–Guest PropertyJournal of the American Chemical Society, 2008
- Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular ChemistryAccounts of Chemical Research, 2003