Anions play some vital roles in the environment and in biological systems. In order to mitigate those problems, the field of anion encryption has raised attention over decades and has been developing with diverse receptors capable of hosting different anions in solution and solid state. Among the various systems, macrocyclic polyamines are promising because they carry positive charge through protonation and mimic many biological polyamines. Polyamine macrocycles with benzene spacers are effective anion receptors under protonation in water. Consequently we have become interested in polyamine macrocycles with heteroaromatic spacers to figure out the role of the spacer to anion binding. And so during the course of our studies, a polyazamacrocycle was synthesized using 2,6-pyridinedicarboxaldehyde spacers and N-methyl-2,2'-diaminodiethylamine linkage from Schiff base condensation followed by reduction. The receptor was studied for anions (F?, Cl?, Br?, I?, NO3?,ClO4?, SO42?, H2PO4?) by 1H NMR spectroscopy technique in water and single crystal X-ray diffraction method. The 1H NMR titration studies reveal that the receptor forms a 1:1 complex with the anion, showing the highest binding constant with sulfate. In this poster, binding studies in both solution and solid will be presented.Acknowledgement:  The National Science Foundation is acknowledged for a CAREER award (CHE-1056927) to MAH. NMR core facility at Jackson State University was supported by the National Institutes of Health (G12RR013459).

Synthesis and anion binding studies of pyridine-based macromonocyclic ployamine

247th National Meeting (2014)

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