Collect. Czech. Chem. Commun. 2004, 69, 885-896

Photophysical Characterisation, Metal Ion Binding and Enantiomeric Recognition of Chiral Ligands Containing Phenazine Fluorophore

Luisa Stella Dolcia, Péter Huszthyb,*, Erika Samuc, Marco Montaltia, Luca Prodia,* and Nelsi Zaccheronia

a Università degli Studi di Bologna, Dipartimento di Chimica "G. Ciamician", Via Selmi 2, I-40126, Bologna, Italy
b Institute for Organic Chemistry, Budapest University of Technology and Economics, and Research Group for Alkaloid Chemistry, Hungarian Academy of Sciences, H-1521 Budapest, P.O. Box 91, Hungary
c EGIS Pharmaceuticals Ltd., Budapest, P.O. Box 100, H-1437 Budapest, Hungary


Enantiomerically pure dimethyl- and diisobutyl-substituted phenazino-18-crown-6 ligands bind metal and ammonium ions and also primary aralkylammonium perchlorates in acetonitrile with high affinity, causing pronounced changes in their luminescence properties. In addition, they show enantioselectivity towards chiral primary aralkylammonium perchlorates. The possibility to monitor the binding process by photoluminescence spectroscopy can gain ground for the design of very efficient enantioselective chemosensors for chiral species. The observed changes in the photophysical properties are also an important tool for understanding the interactions present in the adduct.

Keywords: Chiral crown compounds; Fluorescence spectroscopy; Enantiomeric recognition; Chemosensors; Supramolecular chemistry; Macrocycles; Crown ethers; Phenazines.

References: 36 live references.