Self-assembly of fluorine-containing [2]catenanes based on donor–acceptor interaction

Three novel [2]catenanes in which four or eight fluorine atoms are incorporated into one or two of the phenylene linkers of the tetracationic cyclophanes have been synthesized based on the donor–acceptor interaction principle between the hydroquinone and dipyridinium subunits. Although the introduction of fluorine atoms markedly reduces the assembling efficiency of the [2]catenanes, the existence of fluorine atoms substantially increases the donor–acceptor interaction between the hydroquinone and bipyridiniums of the corresponding [2]catenanes. Two novel fluorine-containing tetracationic cyclophanes have also been synthesized.