Syntheses of three-dimensional catenanes under kinetic control

Autor: 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
Rok vydání: 2022
Předmět:
Zdroj: Proceedings of the National Academy of Sciences of the United States of America. 119(12)
ISSN: 1091-6490
Popis: 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.
Databáze: OpenAIRE