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Rotaxane Formation under Thermodynamic Control

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posted on 1999-10-13, 00:00 authored by Stuart J. Cantrill, Stuart J. Rowan, J. Fraser Stoddart
Thermodynamic control operates in the synthesis of a [2]rotaxane based upon the dibenzylammonium ion/crown ether recognition motif. When dibenzo[24]crown-8 is added to an acetonitrile solution containing a diimine dumbbell-like component, the dynamic nature of the system (i.e., imine hydrolysis/reformation) offers the ring component access to the NH2+ center, allowing the self-assembly of the corresponding “dynamic” [2]rotaxane to occur. The “fixing” of this [2]rotaxane can be achieved upon reduction of the imine bonds, affording a kinetically inert [2]rotaxane.