Synthesis and functions of macrocycles utilizing self-assembling

Abstract

Tandem Claisen rearrangement of various kinds of isobutenyl bis (aryl) ether derivatives can give rearranged-products which have plural hydroxy groups. Bis(benzaldehyde)- and bis(benzoyl chloride) derivatives of them prepared in high yields can react with amine compounds to give diimines and diamides, respectively. The reactions with diamines gave selectively either 1:1 or 2:2 macrocycles with self-assembly in high yields without high-dilution conditions. Furthermore, bis (benzaldehyde) derivatives react with tris (2-aminoethyl) amine in the presence of metal ions such as lanthanides to give a 3:2 three dimensional macrobicycle as a self-organized product in moderate yield. On the other hand, the reaction of bis(benzoyl chloride) derivative with p-phenylenediamine gives a 2:2 macrocycle predominantly, where hydrogen bond formation in the reaction process plays an important role. Thus, the self-assembled combination of bis (benzaldehyde)- and bis(benzoyl chloride) derivatives with diamines either in the presence or in the absence of metal ions could result in forming specific macrocycles, spontaneously.