Can aromaticity be a kinetic trap? Example of mechanically interlocked aromatic [2-5]catenanes built from cyclo[18]carbon

Nikita Fedik; Maksim Kulichenko; Dmitriy Steglenko; Alexander I Boldyrev

doi:10.1039/c9cc09483k

Can aromaticity be a kinetic trap? Example of mechanically interlocked aromatic [2-5]catenanes built from cyclo[18]carbon

Chem Commun (Camb). 2020 Mar 4;56(18):2711-2714. doi: 10.1039/c9cc09483k. Epub 2020 Feb 5.

Authors

Nikita Fedik¹, Maksim Kulichenko, Dmitriy Steglenko, Alexander I Boldyrev

Affiliation

¹ Department of Chemistry and Biochemistry, Utah State University, 0300 Old Main Hill, Logan, UT 84322-0300, USA. a.i.boldyrev@usu.edu.

PMID: 32022006
DOI: 10.1039/c9cc09483k

Abstract

The unusual stability of cyclo[18]carbon arising from its aromaticity might be used to provide the kinetic trapping needed in the design of interlocked systems. The kinetic barrier separating the interlocked rings and the chemically bonded complex is about 30 kcal mol^-1. In addition, the rings can slide freely, which is a promising property for the design of molecular gears and motors.