Synthesis and characterization of macrocyclic compounds with a hydroxyl functional group

A novel 1+1] Schiff-base macrocyclic compound 3 has been synthesized from precursor 1, 1,3-bis(2'-formylphenoxy)-2-propanol, and precursor 2, resorcinol-bis(4-aminophenyl)ether, via condensation and cyclizaction using Ba2+ as template. The macrocycle 3 was further reduced giving saturated macrocycle 4. The structures of 3 and 4 were characterized by elemental analysis, 1H NMR, IR, and MS spectra, and their structures were determined via single crystal X-ray diffraction studies. X-ray diffraction analysis revealed that the macrocyclic compound 3 has a folded conformation, and the corresponding reduced product 4 adopts a twisted and folded conformation due to its flexible nature.