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Bob Dylan's greatest hits. The rotaxanes are formed within a few minutes simply through mixing the components in solution at room temperature and they can be isolated through removal of the solvent or precipitation.
The Copper I template system based on 2,9-diphenyl-1,phenanthroline dpp ligands,[ 1 ] introduced by Sauvage and co-workers in the s,[ 2 ] revolutionized the synthesis of catenanes, rotaxanes, and knots[ 3 ] and has remained a mainstay of interlocked molecule synthesis for three decades. The reason that the yields are so high for an assembly process that features bidentate ligand motifs on each component is that the rotaxane is the only possible product that allows maximal site occupancy[ 2a , 12 ] with a strict equimolar ratio of ligands and metal ion, and the reaction is carried out under thermodynamic control.
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Signals from traces of aldehyde 2 in a are colored gray. Cu I -mediated assembly of rotaxane 4, rotaxane 9, and imine thread 5. As well as shielding of several of the thread protons e. The reduced motif can be used to assemble rotaxanes under kinetic control through a threading-and-stoppering procedure see the Supporting Information.source
Dynamic Chirality: Molecular Shuttles and Motors | SpringerLink
Methods to directly reduce the imine rotaxanes to amine rotaxanes are currently being developed in our laboratory. X-Ray crystal structures of the assembly motif in pseudorotaxanes 6 and 7. Hydrogen atoms, counterions, and solvent molecules are omitted for clarity. Carbon atoms of the macrocycle are shown in light blue, carbon atoms of the threads gray; oxygen atoms red, nitrogen atoms dark blue, and copper atoms orange.
In conclusion, we have discovered a simple and effective ligand set for the assembly of imine-based rotaxanes around copper I ions. The reactions proceed with high yield within a few minutes at ambient temperature and provide a readily accessible alternative to the classic Cu I — dpp 2 rotaxanes.
We anticipate that this facile method may find application in the synthesis of a range of interlocked molecular structures. A right-handed helix is described as P or plus , a left-handed one as M or minus.
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Asked 3 years, 3 months ago. Active 2 years, 4 months ago. Viewed times. Mislow, one of the great, modern-day stereochemists, got the ball rolling. If you google "Mislow, trefoil chirality" you'll get a number of useful links, but again, it's involved.
The above knotane is right-handed, so it should be P. For more complex molecular knots such simple rules most likely will fail. Do you have any source applying the this system trefoil knot? However, I don't know any source where the system is applied to the molecular trefoil knot.