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 |
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| Authors: | Júlia Kertész Péter Huszthy Attila Kormos Ferenc Bertha Viola Horváth George Horvai |
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| Affiliation: | 1. Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, H-1521 Budapest, PO Box 91, Hungary;2. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, PO Box 91, Hungary;3. Egis Pharmaceuticals PLC, H-1475 Budapest, PO Box 100, Hungary;4. Research Group for Technical Analytical Chemistry of the Hungarian Academy of Sciences, H-1521 Budapest, PO Box 91, Hungary;5. Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, H-1521 Budapest, PO Box 91, Hungary |
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| Abstract: | 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. |
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