Synthesis of new optically active acridino-18-crown-6 ligands and studies of their potentiometric selectivity toward the enantiomers of protonated 1-phenylethylamine and metal ions

Starting from commercially available and relatively inexpensive chemicals, new enantiopure diisobutyl- and dioctyl-substituted acridino-18-crown-6 ether-type ligands [( R,R)- 3] and [( R,R)- 4], respectively were prepared. The two lipophilic isobutyl [( R,R)- 3] and octyl [( R,R)- 4] groups on the s...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2009-12, Vol.20 (24), p.2795-2801
Main Authors: Kertész, Júlia, Huszthy, Péter, Kormos, Attila, Bertha, Ferenc, Horváth, Viola, Horvai, George
Format: Article
Language:English
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Summary:Starting from commercially available and relatively inexpensive chemicals, new enantiopure diisobutyl- and dioctyl-substituted acridino-18-crown-6 ether-type ligands [( R,R)- 3] and [( R,R)- 4], respectively were prepared. The two lipophilic isobutyl [( R,R)- 3] and octyl [( R,R)- 4] groups on the stereogenic centers of these macrocycles made it possible to use them as potentiometric sensor molecules when incorporated into plasticized PVC membrane electrodes. Ligand ( R,R)- 3 showed appreciable enantioselectivity toward the enantiomers of 1-phenylethylammonium chloride while macrocycle ( R,R)- 4 exhibited a high selectivity toward the silver ion.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2009.11.011