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Synthesis and Anion Binding Properties of a Novel 1, 8-dipyrrolecarbazole Schiff-base

New anion receptor N1, N8-bis[1H-pyrro-2-yl-methylidene]-3, 6-dichloro-9H-carbazole-1, 8-diamine (3) was synthesized and its binding properties towards anions (Cl–, Br–, AcO– and H2PO4–) investigated by UV/Vis spectroscopy. In order to find the most stable structure of receptor 3, geometries of all possible isomers of 3 were optimized by the DFT/B3LYP method. It has been determined that receptor 3 forms complexes with a 1:1 stoichiometry with all the studied anions and no significant selectivity with respect to anion geometry was found. However, 1, 8- dipyrrolecarbazole Schiff-base 3 binds oxoanions (H2PO4– and AcO–) more strongly than spherical halogenide (Cl– and Br–) anions.

anion receptors ; carbazole ; pyrrole ; Schiff-base

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