Krishna Damodaran - Fluorescent Acridine-Based Receptors for H2PO4–

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      Publication Details (including relevant citation   information):

      J. Org.   Chem., 2012, 77, 490.


      Two new pseudopeptidic molecules (one macrocyclic and one open   chain) containing an acridine unit have been prepared. The   fluorescence response of these receptors to a series of acids was   measured in CHCl3. Receptors are selective to   H2PO4 versus   HSO4, and an even higher selectivity is   found over other anions such as Cl, Br,   CH3COO, and CF3COO.   We show that the macrocyclic receptor is more selective for   H2PO4 than the related open   chain receptor. The supramolecular interactions of triprotonated   receptors with different anions have been modeled in silico and   have been studied by different experimental techniques. Optimized   geometries obtained by computational calculations agree well with   experimental data, in particular fluorescence experiments,   suggesting that the selective supramolecular interaction takes   places through coordination of the anions to the triprotonated   form of the receptor.

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