Bridging Rotaxanes' Wheels—Cyclochiral Bonnanes

Abstract

Building bridges: The wheels of [3]rotaxane were intramolecularly tethered to yield the first member of cyclochiral, interlocked architectures named “bonnanes” (after the city Bonn, Germany; see scheme). The enantiomers and meso form were separated on an immobilized chiral phase and characterized.

Chirality in rotaxanes and catenanes

“…Vögtle and co-workers later reported chiral [3]rotaxane derivatives in which the macrocycles are linked by a covalent bridge which they christened “Bonnanes”. 119 …”

Mechanically interlocked molecular handcuffs

“…Indeed the most common form of molecular handcuffs are (2)handcuff [2]rotaxanes. An alternative name for this type of bridged macromolecule was proposed by Vögtle, 11 who pioneered some of the early work into handcuff rotaxanes. He suggested 'Bonnanes' aer the city of Bonn in which they were based, the former bridge capital of Germany, to reect the bridge between the pair of macrocycles.…”

“…One of the rst reported syntheses of a (2)handcuff [2]rotaxane came from the Vögtle group in 2006 who were investigating covalent reactions of rotaxanes for further preparative chemistry. 11 Vögtle and coworkers rst prepared a [3]rotaxane that consisted of two sulfonamide containing macrocycles about a single axle (Fig. 3a).…”

Precision synthesis of linear oligorotaxanes and polyrotaxanes achieving well-defined positions and numbers of cyclic components on the axle

“…Vo ¨gtle et al reported an early example of the iterative method to synthesize oligorotaxanes in 1999. 66,67 They applied stepwise reactions to prepare an axle molecule bearing a bulky capping moiety. The oligorotaxanes were then synthesized by exploiting the hydrogen bonding between the macrocycles and amide moieties of the axle components.…”