Syntheses of three-dimensional catenanes under kinetic control

Yong Wu, Qing Hui Guo*, Yunyan Qiu, Jacob A. Weber, Ryan M. Young, Laura Bancroft, Yang Jiao, Hongliang Chen, Bo Song, Wenqi Liu, Yuanning Feng, Xingang Zhao, Xuesong Li, Long Zhang, Xiao Yang Chen, Hao Li, Michael R. Wasielewski, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Although catenanes comprising two ring-shaped components can be made in large quantities by templation, the preparation of three-dimensional (3D) catenanes with cage-shaped components is still in its infancy. Here, we report the design and syntheses of two 3D catenanes by a sequence of SN2 reactions in one pot. The resulting triply mechanically interlocked molecules were fully characterized in both the solution and solid states. Mechanistic studies have revealed that a suit[3]ane, which contains a threefold symmetric cage component as the suit and a tribromide component as the body, is formed at elevated temperatures. This suit[3]ane was identified as the key reactive intermediate for the selective formation of the two 3D catenanes which do not represent thermodynamic minima. We foresee a future in which this particular synthetic strategy guides the rational design and production of mechanically interlocked molecules under kinetic control.

Original languageEnglish (US)
Article numbere2118573119
JournalProceedings of the National Academy of Sciences of the United States of America
Volume119
Issue number12
DOIs
StatePublished - Mar 22 2022

Keywords

  • Cationic cages
  • Mechanically interlocked molecules
  • Nontrivial topologies
  • Suitanes
  • Triple [π...π] interactions

ASJC Scopus subject areas

  • General

Fingerprint

Dive into the research topics of 'Syntheses of three-dimensional catenanes under kinetic control'. Together they form a unique fingerprint.

Cite this