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.

Graphical abstractA novel [1+1] Schiff-base macrocyclic compound 3 has been synthesized by the condensation reaction of precursor dialdehyde, 1,3-bis(2′-formylphenoxy)-2-propanol, with the diamine, resorcinol-bis(4-aminophenyl)ether. The macrocycle 3 has a folded conformation, and the corresponding reduced product 4 adopts a twisted and folded conformation. The crystal structures of 3 and 4 were determined via X-ray single crystal diffraction analysis.Figure optionsDownload full-size imageDownload as PowerPoint slide