Abstract The synthesis of nine macrocyclic polyether-and polythioether-diesters 9–13 and dithioesters 14–17 derived from 1, 10-phenanthroline-2, 9-dicarboxylic acid are reported. The macrocycles were prepared under conditions of high dilution in the absence of metal templates in consistently good yields and their structures were confirmed by 1 H and 13 C nmr spectroscopy. A macrocyclic phenanthroline-pyridine tetraester 18 is also recorded.