Details

Autor(en) / Beteiligte

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

Titel

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+.