Synthesis 2015; 47(16): 2485-2495
DOI: 10.1055/s-0034-1380814
paper
© Georg Thieme Verlag Stuttgart · New York

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

Ole Beyer
Christian-Albrechts-Universität zu Kiel, Otto-Diels-Institut für Organische Chemie, Olshausenstraße 40, 24098 Kiel, Germany   Email: luening@oc.uni-kiel.de
,
Britta Hesseler
Christian-Albrechts-Universität zu Kiel, Otto-Diels-Institut für Organische Chemie, Olshausenstraße 40, 24098 Kiel, Germany   Email: luening@oc.uni-kiel.de
,
Ulrich Lüning*
Christian-Albrechts-Universität zu Kiel, Otto-Diels-Institut für Organische Chemie, Olshausenstraße 40, 24098 Kiel, Germany   Email: luening@oc.uni-kiel.de
› Author Affiliations
Further Information

Publication History

Received: 26 March 2015

Accepted after revision: 18 April 2015

Publication Date:
17 June 2015 (online)


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.

Supporting Information

 
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