title: Synthesis of [3]rotaxanes that utilize the catalytic activity of a macrocyclic phenanthroline-Cu Complex: remarkable effect of the length of the axle precursor.
abstract: [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 catalytic activity of a macrocyclic phenanthroline-Cu complex was utilized to thread the two axle components inside the ring. The alkyne compound with chain of 15 or 20 methylene groups gave [3]rotaxanes in high yields, whereas the axle with a chain of six methylene groups afforded a [3]rotaxane in very poor yield. We also examined the effect of the ring size on the synthesis of [3]rotaxanes. [3]Rotaxanes were not isolated when a macrocyclic phenanthroline compound with a smaller ring size was used.
authors.affiliation: Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan).
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Yamashita
authors.forename: Yuichiro
authors.initials: Y
authors.lastname: Mutoh
authors.forename: Ryu
authors.initials: R
authors.lastname: Yamasaki
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kasama
authors.forename: Shinichi
authors.initials: S
authors.lastname: Saito
mesh_terms: D003300:Copper / Q000737:chemistry*; D008958:Models, Molecular; D010618:Phenanthrolines / Q000737:chemistry*; D043862:Rotaxanes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010618:Phenanthrolines; D043862:Rotaxanes; D003300:Copper
keywords: NMR spectroscopy; copper; dimerization; macrocycles; rotaxanes