Simulation of [2]rotaxane and [2]catenane compounds containing fullerene fragments. Influence of the fullerene moiety

Abstract

A direct covalent bond joins fullerene molecules to chains which form [2]rotaxane and [2]catenane molecules. The chains are directly connected to the fullerene surface by a covalent CC bond, enabling all electronic riches from fullerenes to be shared with the chains. We carried out this simulation in two stages; the first consisted in designing the “ball and chain” molecules in order to reveal the nature of the bonds and the frontier molecular orbitals. During this stage, notoriously strong dispersion bonds are formed between the fullerene sphere and the body of the chain. During the second stage, [2]rotaxane and [2]catenane are formed. Fullerenes significantly influence the resultant compounds and we also discuss their thermodynamic stability and electronic behavior.