@article{eprints2167,
       publisher = {American Chemical Society},
            note = {PMID: 18841919},
         journal = {Journal of Organic Chemistry},
          author = {Carla Bazzicalupi and Andrea Bencini and Antonio Bianchi and Claudia Borri and Andrea Danesi and Enrique Garcia-Espan?a and Claudia Giorgi and Barbara Valtancoli},
          volume = {73},
           pages = {8286--8295},
          number = {21},
           title = {Polyfunctional recognition of pyridinedicarboxylate anions with macrocyclic polyamine receptors containing heteroaromatic groups},
            year = {2008},
             url = {http://eprints.imtlucca.it/2167/},
        abstract = {The interaction of the biologically relevant anions deriving from the six pyridinedicarboxylic acids (H2PDC) with two macrocyclic receptors containing a pentamine chain and a bipyridine (1) or a phenanthroline (2) moiety, as well as with the aliphatic analogue 21aneN7 (3), was studied by means of spectroscopic methods (UV?vis, NMR) and potentiometric titrations affording the stability constants of the adducts formed. All three receptors form stable complexes with the substrates thanks to the formation of several salt bridges and hydrogen bond contacts, as observed in the crystal structure of the H83(2,6-PDC)4?H2O?0.5EtOH solid compound. Additional {\ensuremath{\pi}}-stacking interactions between the aromatic moieties of substrates and receptors enhance the stability of complexes with 1 and 2. Compounds 1 and 2 show a marked selectivity toward 2,6- pyridinedicarboxylate anions. In particular, 1 is able to perform a very efficient recognition of these species in the presence of 2 and 3. Molecular modeling calculations suggested that such recognition ability of 1 can be ascribed to a superior structural and electrostatic complementarity with the substrate compared to 2 and 3. }
}