A Convenient Access to a [2]Rotaxane Proton Shuttle by Using a Fluorous Ponytail

Dedicated to Professor Bernd Giese on the occasion of his 75th birthday

Abstract

The properties of rotaxanes and their constituents, ring and axle, sometimes do not differ much from one another resulting in tedious workup. In the case of a rotaxane designed to shuttle protons across a biological membrane (3–4 nm), molecular weight, shape, and functional groups of axle and rotaxane are similar. But when the macrocyclic ring of the rotaxane carries a fluorous residue, the fluorous effect distinguishes the rotaxane from the axle because the latter carries no fluorine atoms. This concept has been exploited to synthesize a [2]rotaxane in which the macrocyclic ring is protonable and the axle contains a permanent positive charge. Upon protonation/deprotonation of the macrocycle, a shuttling process is induced, which can lead to the transport of protons.

Key words

rotaxane - trapping - macrocycles - proton transport - fluorine

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