A new bistable rotaxane, consisting of a 2,2'-bipyridine-containing thread and a ring incorporating both a bidentate chelate and a tridentate fragment, has been prepared; this complex undergoes an electrochemically driven pirouetting motion of the ring around the axis which takes place on the millisecond timescale, i.e. several orders of magnitude faster than the other copper-based machines previously described.
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Optically active two and three layer nitrogen ligands were synthesized by reacting the N-BOC-protected aminoalcohols (1S,2S)-2-amino-1 -phenyl-1,3-propanediol and (S)-2-amino-1,4-butanediol with chloromethyl-benzoic acid chlorides. Expansion was carried out at the chlo-romethyl substituents via nucleophilic substitution with N-methylated (R)-1-phenylethylamine. The deprotected substances were N-benzylated and reacted with 6,6′-bis(bromomethyl)-2,2′-bipyridine to give the new optically active expanded bipyridine ligands.
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