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Fluorescent phenanthridine-based calix[4]arene derivatives: synthesis and thermodynamics of complexation reactions with metal cations

Calixarenes are macrocyclic oligomers consisted of four or more phenolic residues linked by methylene groups in ortho position. Depending on their size and substituents at lower and/or upper rim, these compounds have been found to be very efficient receptors for various chemical species. Those bearing suitable binding sites as well as fluorescent moieties can be considered as very sensitive ion sensors due to the high sensitivity of fluorescence spectroscopy. In the scope of this work, two fluorescent phenanthridinebased calix[4]arene derivatives L1 and L2 (Figure 1) were designed and prepared. Their binding affinities towards alkali, alkaline earth, and transition metal cations in various organic solvents (acetonitrile, methanol, ethanol, N, N- dimethylformamide, dimethyl sulfoxide) were investigated by means of UV, fluorimetry, NMR, and isothermal titration calorimetry. The obtained results were discussed regarding the structural characteristics of the studied calixarene derivatives and solvation abilities of the solvents used.

calix[4]arene ; phenantridine ; metal cation ; fluorescence

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