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Bis-8-hydroxyquinoline-Armed Diazatrithia-15-crown-5 and Diazatrithia-16-crown-5 Ligands: Possible Fluorophoric Metal Ion Sensors
Ist Teil von
Journal of organic chemistry, 2001-07, Vol.66 (14), p.4752-4758
Ort / Verlag
United States: American Chemical Society
Erscheinungsjahr
2001
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
The synthesis and preliminary photophysical properties of a series of diazatrithia-15-crown-5 and diazatrithia-16-crown-5 ligands containing two 8-hydroxyquinoline sidearms are reported. The ligands were prepared by a two-step process. First, diazatrithiacrown ethers 11 and 12 were prepared by treating bis(α-chloroamide) 5 with various dimercaptans followed by reduction using a boron−THF complex. Hydroxymethyl-substituted macrocycle 12 was rearranged to hydroxy-substituted diazatrithia-16-crown-5 in refluxing aqueous HCl. Macrocyclic diamines 11−13 were converted to either 5-chloro-8-hydroxyquinolin-7-ylmethyl-substituted diazatrithiacrown ethers 14−16 by a Mannich aminomethylation reaction or to 8-hydroxyquinolin-2-ylmethyl-substituted diazatrithiacrown ethers 17−19 by reductive amination using 8-hydroxyquinoline-2-carboxaldehyde. Preliminary photophysical studies show that ligands 16 and 19 exhibit increased fluorescence in the presence of Zn2+, indicating that these ligands could be chemical sensors for Zn2+.
Sprache
Englisch
Identifikatoren
ISSN: 0022-3263
eISSN: 1520-6904
DOI: 10.1021/jo0017584
Titel-ID: cdi_crossref_primary_10_1021_jo0017584
Format
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