Cubane-1,3-dicarboxamides as structural isosteres for isophthalamides in hydrogen bond templated interlocked molecules.

The synthesis and characterization of the first examples of cubane containing interlocked molecules are reported. Catenanes and rotaxanes have been prepared by hydrogen bond templation with cubane-1,3-dicarboxamides replacing isophthalamide motifs.

Synthesis of a [2]catenane by ring closing metathesis of a [2]rotaxane prepared by crown ether active templation.

The high yielding synthesis and spectral characterization of a [2]catenane prepared by Grubbs catalyzed ring closing metathesis of a [2]rotaxane prepared by crown ether active template synthesis is described.

Rapid synthesis of hydrogen bond templated handcuff rotaxanes.

The rapid synthesis of hydrogen bond templated handcuff rotaxanes is described. The isolated rotaxanes were characterized by NMR and IR spectroscopies and high resolution mass spectrometry. This report represents a rare demonstration of preparing (2)handcuff [2]rotaxanes by covalently linking separate axles threaded through the rings of a bis-macrocycle by use of the copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction.

A pyridine--oxide catenane for cation recognition.

The rapid preparation of a pyridine--oxide containing [2]catenane is described. The [2]catenane was characterized by NMR spectroscopy, mass spectrometry and X-ray single crystal structure determination. H NMR titration experiments reveal the [2]catenane may be reversibly protonated, as well as an ability to bind lithium cations more strongly than sodium cations.

Hydrogen bond templated synthesis of catenanes and rotaxanes from a single isophthalic acid derivative.

Hydrogen bond templated [2]catenanes and [2]rotaxanes have been synthesized using azide precursors derived from a single isophthalic acid derivative precursor. The interlocked molecules were prepared using either stoichiometric or near stoichiometric amounts of macrocycle and CuAAC "click" precursors, with yields of up to 70% for the mechanical bond formation step. Successful preparation of the interlocked structures was confirmed by NMR spectroscopy and mass spectrometry, with detail of co-conformational behaviour being elucidated by a range of H NMR spectroscopic experiments.