Exploration of a Method for the Preparation of 1,10-phenanthroline Derived Chemosensors
Northrup, J. D.
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The exploration of a suitable method for the formation of 5-hydroxy-6-(2- aminopyridine)-1,10-phenanthroline is detailed in the following report. The hope was that 5-hydroxy-6-(2-aminopyridine)-1,10-phenanthroline would prove to be a better sensitizing ligand than 1,10-phenanthroline and thus a more efficient chemosensor for the detection of nerve agents such as Sarin gas. In the first reaction, 1,10-phenanthroline was reacted with aqueous sodium hypochlorite to produce 5,6-epoxy-1,10-phenanthroline with an 80%yield. This epoxide was subsequently reacted - employing a Lewis Acid (either [Mg(C104)2] or [Yb(OTf)3]) as a catalyst - with the nucleophile 2-aminopyridine to form 5-hydroxy-6-(2-aminopyridine)-1,10-phenanthroline. The product from this second reaction was not able to be isolated from the reaction mixture; therefore, its efficacy as a sensitizing ligand for nerve agent chemosensors could not be tested.