Synthesis and Characterization of N-ethyl-(4-methyl-6-nitro-quinolin-2-yl)-amine and N-cyclohexyl-(4-methyl-6-nitro-quinolin-2-yl)-amine

Melody Heiskell
April 2002



science theses

Abstract

Since the 1980s, organic molecules have gained importance in the search for new nonlinear optical materials. Previous research revealed that specific organic functional groups, ones that can be easily added to organic materials, are correlated with good nonlinear optical responses. As a result, organic chemists are able to tailor molecules with favorable nonlinear optical properties. Synthesis goals of this research aimed to incorporate organic functional groups that could potentially increase the nonlinear optical properties of N-alkyl-(4-methyl-6-nitroquinolin-2-yl)-amine. Several amines were chosen to add as the "N-alkyl" portion of the N-alkyl-(4-methyl-6-nitroquinolin-2-yl)-amine. Another research goal was to incorporate metal ions in this molecule, in order to increase nonlinear optical properties. Initially, technical and synthesis difficulties impeded the synthesis of new organometallic compounds. Yet, after many retrials, the problems in the basic synthesis schematic were finally solved. Molecular structures of N-ethyl- (4-methyl-6-nitroquinolin-2-yl)-amine and N-cyclohexyl-(4-methyl-6-nitroquinolin-2-yl) -amine were characterized by x-ray crystallography and prove that the new synthesis methods outlined in this research are effective and reproducible. Future research in the synthesis of organometallic nonlinear optical materials should encounter fewer complications with the aid of these discoveries.


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