Synthesis and recognition properties of α-d-glucose-based fluorescent crown ethers incorporating an acridine unit

Rapi, Zsolt and Bakó, Péter and Keglevich, György and Baranyai, Péter and Kubinyi, Miklós and Varga, Olívia (2014) Synthesis and recognition properties of α-d-glucose-based fluorescent crown ethers incorporating an acridine unit. JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY , 2014. pp. 1-9. ISSN 1388-3127, (eISSN: 1573-1111)

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Abstract

Two new chiral glucopyranoside-based crown ethers incorporating acridine fluorescent signalling units, 15-membered ligand 1 and 21-membered ligand 2 were synthesized. Their complexation properties toward alkali and alkali earth metal ions, and their enantioselectivity towards chiral ammonium salts were studied by absorption and fluorescence spectroscopic experiments. Macrocycle 1 formed 1:1 complexes with all the metal ions selected and the stability constants were low (lg K < 2.3). The cavity-size of 2 allowed only the complexaton of organic ammonium ions. Crown 2 showed chiral discrimination in case of all the four ammonium salts used as model guest compounds; the highest enantioselectivity (K(R)/K(S) ~3) was observed for the enantiomers of phenylethyl ammonium perchlorate. Ligand 2 forms much more stable complexes with metal ions; the highest stability constant was obtained for the Ca2+ complex (lg K = 6.15). The coordination of metal ions by ligand 2 was accompanied by marked fluorescence enhancement, whereas the binding of ammonium ions by the same species resulted in significant fluorescence quenching. © 2014 Springer Science+Business Media Dordrecht.

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