Recent Advances in Halogen Bonded Assemblies with Resorcin[4]arenes

Chem Rec. 2021 Feb;21(2):386-395. doi: 10.1002/tcr.202000140. Epub 2020 Dec 23.

Abstract

Resorcinarenes are cavity-containing compounds when in the crown conformation, from the calixarene family of concave compounds. These easy to synthesize macrocycles can be decorated at the upper rim through the eight hydroxyl groups and/or the 2-position of the aromatic ring. They are good synthons in supramolecular chemistry leading to appealing assemblies such as open-inclusion complexes, capsules and tubes through multiple weak interactions with various guests. Halogen bonding (XB) is a highly directional non-covalent interaction by an electron-deficient halogen atom as a donor that interacts with a Lewis base, the XB acceptor. This tutorial review provides an overview of recent advances in halogen-bonded assemblies based on resorcinarenes and their derivatives, specifically focusing on discrete and capsular assemblies.

Keywords: capsules; cavitands; discrete assemblies; halogen bond; resorcinarenes.