Bis-8-hydroxyquinoline-Armed Diazatrithia-15-crown-5 and Diazatrithia-16-crown-5 Ligands: Possible Fluorophoric Metal Ion Sensors

Autor:	Reed M. Izatt, Saowarux Fuangswasdi, R. T. Bronson, Sang Chul Lee, Krzysztof E. Krakowiak, Paul B. Savage, Jerald S. Bradshaw
Rok vydání:	2001
Předmět:	Metal chemistry.chemical_compound Aqueous solution chemistry 15-Crown-5 visual_art Organic Chemistry Polymer chemistry visual_art.visual_art_medium 8-Hydroxyquinoline Fluorescence Reductive amination
Zdroj:	The Journal of Organic Chemistry. 66:4752-4758
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo0017584
Popis:	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(alpha-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 Zn(2+), indicating that these ligands could be chemical sensors for Zn(2+).
Databáze:	OpenAIRE
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