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Synthesis of diazadibenzo‐18‐crown‐6 ligands with appended chromophoric and fluorophoric groups as potential metal ion chemosensors
Author(s) -
Xue GuoPing,
Savage Paul B.,
Krakowiak Krzysztof E.,
Izatt Reed M.,
Bradshaw Jerald S.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380631
Subject(s) - chemistry , crown ether , 18 crown 6 , reagent , amination , quinoline , reductive amination , metal , metal ions in aqueous solution , combinatorial chemistry , ligand (biochemistry) , aqueous solution , ion , polymer chemistry , organic chemistry , biochemistry , receptor , catalysis
Six new diazadibenzo‐18‐crown‐6 ligands substituted with two each of 8‐hydroxyquinoline (7), 8‐amino‐quinoline (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 ).