Six new diazadibenzo-18-crown-6 ligands substituted with two each of 8-hydroxyquinoline (7), 8-aminoquinoline (attached through its C-2 or C-7 position) (12 and 13). 8-methoxyquinoline (18), 5-chloro-8-methoxyquinoline (19), and dansylamidoethyl (21) side arms were synthesized as potential metal ion chemosensors and potential reagents for the selective extraction of certain metal ions from aqueous solutions. Ligands 7, 12, 13, 18, and 19 were synthesized by reductive amination of diazadibenzo-18-crown-6 (5) and the appropriate quinolinecarboxaldehydes. Bis(dansylamidoethyl)-substituted ligand 21 was synthesized by treating diazacrown ether 5 with N-dansylaziridine (20).