Portal de Periódicos da CAPES

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

2001; American Chemical Society; Volume: 66; Issue: 14 Linguagem: Inglês

10.1021/jo0017584

1520-6904

R. Todd Bronson, Jerald S. Bradshaw, Paul B. Savage, Saowarux Fuangswasdi, Sang Chul Lee, Krzysztof E. Krakowiak, Reed M. Izatt,

Analytical Chemistry and Sensors

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+).