Preparation of a New Macrocycle as Nano machine

Due to important role of aza crown compounds in large number of applications, there is continuous interest in their preparation and their corresponding macrocyclic diamides. These compounds have wide applications in chemistry, nano technology (such as: nano machine, nano catalysis, nano material, nano filters,…). A nano machine is an assembly of a discrete number of supramolecular components designed to perform mechanical – like movements as a consequence of appropriate external stimuli. Our purpose is preparation of a part of nano machines are based on interlocked macrocycle named rotaxanes, catenanes, pseudorataxane and knots. The sulfoxide (1) was prepared by reaction p-Cresol with SOCl2 in dry dichloromethane in 65% yield. Then bisphonle (2) was prepared with reduction compound (1) in Zn powder and acetic acid. Treatment of bisphenole (2) with methyl chloroacetate in the presence of K2CO3 and KI at refluxed by dry acetone gave dimethyl ester (3) in 98% yield. Macrocyclic diamide (4) in 70% yield was prepared by diamidation of diester (3) with triethylene tetra amine, and then purified with recrystaliztion from propyl alchole.

Keywords:

Nano machine , Catenane , Macrocyclic diamid