A tri(ethylene glycol)-tethered Morita-Baylis-Hillman dimer in the formation of macrocyclic crown ether-paracyclophane hybrid structures

A Morita-Baylis-Hillman acetate was dimerized by a click-chemistry Copper(i)-Catalysed Azide-Alkyne Cycloaddition (CuAAC) reaction employing a tri(ethylene glycol) diazide derivative to obtain a dimeric MBHA derivative. The reaction of this dimeric MBHA derivative with n-butylamine afforded a photoisomerizable macrocyclic crown ether-paracyclophane hybrid architecture that is potentially useful in a large variety of applications as well as those already well-known for crown ethers. A tri(ethylene glycol)-tethered MBHA dimer was synthesized and found to react with n-butylamine leading to the formation of macrocyclic crown ether-paracyclophane hybrid structures that could be modulated by light.