Pseudorotaxanes and rotaxanes from macrocyclic rings incorporating acridinone, 9-phenylacridinium and 9-phenyl-9-methoxy-acridane moieties

Two novel crown ethers incorporating the acridinone and the 9-phenyl-9-methoxy-acridane unit were used to form pseudorotaxanes with the 1,2-bis(4,4′dipyridinium)ethane axle, which are stoppered by the alkylative method to form rotaxanes. The pseudorotaxane formed from the acridane-containing crown was photochemically converted to the corresponding acridinium methoxide thereby releasing the guest. The acridane-containing rotaxane could not be isolated because the preparation conditions formed the acridinium salt.