A new rigid benzene-bridged macrotricyclic ligand

Article abstract of DOI:10.1002/jhet.5570370408

A macrotricyclic ligand composed of two benzene rings connected by four 2,2'-oxydiphenoxide bridges (2) has been prepared by treating 1,2,4,5-tetrakis[2-(2-hydroxyphenoxy)phenoxymethyl]benzene with 1,2,4,5-tetrakis(bromomethyl)benzene in acetonitrile in the presence of potassium carbonate. Ligand 2 is of interest because of its similarity to macrocycle 1 which interacts strongly with cesium ions. The proposed more direct route of treating an excess of 2,2-oxydiphenol with 1,2,4,5-tetrakis(bromomethyl)benzene to prepare 2 did not give the desired macrocycle but gave bis(tribenzo-11-crown-3) (8). An X-ray crystal structure study of 2 showed that the benzene rings which are linked by the four 2,2'-oxydiphenoxide bridges are connected in a nonsymmetric pattern. The structure of 8 was also determined using X-ray diffraction methods, and is reported.