Synthesis and characterization of new rotaxanes from related crown compounds

Abstract

Physical manipulation can be carried out on molecules and cells through the utilization of nanomachines which are machines with nano dimensions. There are different types of nanomachines. Among them, rotaxanes stand out as the most well-known. The term of rotaxane originates from the combination of the Latin words wheel and axis. The application of nanomachines is identifying and measuring the concentration of toxic substances in the environment, targeted drug delivery and cancer diagnosis. The objective of this study is to synthesize and identify several new nanomachines in the form of rotaxanes (internally locked molecules) with nanopharmaceutical properties from the corresponding crown compounds. In the first step, 2,2-dimethylphenol was converted into bisphenol compound (1) in reaction with thionyl chloride. Bisphenol compound (1) was converted into methyl diester compound (2) in reaction with methyl chloroacetate. The methyl diester compound (2) reacts with the appropriate diamine to form the diamide macrocycle compound (3). Rod (4) is prepared from the reaction of diethylene glycol ditosylate, 4,4-bipyridine and a bulk phenol such as 4-tert-butylphenol in DMF. Each of the rings in the presence of the prepared rod leads to the corresponding rotaxane compound (5). Chemical structure of the obtained compounds were established by ¹HNMR, ¹³CNMR, FT-IR and SEM spectroscopic methods.