Synthesis of [3]Rotaxanes that Utilize the Catalytic Activity of a Macrocyclic Phenanthroline-Cu Complex: Remarkable Effect of the Length of the Axle Precursor
[3]Rotaxanes, which consist of one macrocyclic phenanthroline compound and two axle components, were prepared by the oxidative dimerization of an alkyne compound with bulky tris[4′‐cyclohexyl‐(1,1′‐biphenyl)‐4‐yl]methyl blocking group. The catalyticactivity of a macrocyclicphenanthroline–Cucomplex was utilized to thread the two axle components inside the ring. The alkyne compound with chain of 15
We synthesized [2]rotaxanes with a pyrrole moiety from a [2]rotaxane with a 1,3-diynyl moiety. The conversion of the 1,3-diynyl moiety of the axle component to the pyrrole moiety was accomplished by a Cu-mediated cycloaddition of anilines. The cycloaddition reaction was accelerated when the [2]rotaxane was used as the substrate. The effect of the structure of the pyrrole moiety on the rate of the shuttling
[2]Rotaxane with deca(para-phenylene) structure was synthesized in high yield under mild conditions by biaryl coupling mediated by a macrocyclic nickel complex. Deca(para-phenylene)[2]rotaxane was readily soluble, and the optical properties of the compounds were examined in solution.