Thermodynamic control operates in the synthesis of a rotaxane based upon the dibenzylammonium ion/crown ether recognition motif. When dibenzocrown-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" rotaxane to occur. The "fixing" of this rotaxane can be achieved upon reduction of the imine bonds, affording a kinetically inert rotaxane.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry