Theses and Dissertations
Synthesis of Tetraethyl ((2-Amino-1,4-Phenylene)Bis(Methylene)) Bis(Phosphonate): An Intermediate in the Synthesis of Amino-Substituted Conjugated Materials
Date of Award
Master of Science (MS)
Dr. Jose J. Gutierrez
Dr. Evangelia Kotsikorou
Dr. Jason Parsons
Discussed here are the syntheses of the phosphonate precursors for the Wittig-Horner synthesis of poly-phenylene vinylene (PPV) and distyrylbenzene (DSB) derivatives and their respective distyrylbenzene analogs containing amino moieties. The synthesis of the different compounds was achieved through bromination, Michaelis-Arbuzov reaction, reduction of the nitro group with a commercial cobalt sulfide catalyst and sodium borohydride. Preliminary evidence for the synthesis of amino substituted distyrylbenzene and of nitro/alkoxy substituted poly(p-phenylene vinylene) was obtained. Characterization of the products was performed by 1H-NMR. Preliminary results of the synthesis of a novel amino-substituted distyrylbenzene (DSB) are presented. The luminescence of the new DSB was quenched by addition of acid. The luminescence was restored by addition of a base. This was indirect proof that the amino-substituted DSB was synthesized successfully.
Torres Burgueno, Ariel Ivan, "Synthesis of Tetraethyl ((2-Amino-1,4-Phenylene)Bis(Methylene)) Bis(Phosphonate): An Intermediate in the Synthesis of Amino-Substituted Conjugated Materials" (2017). Theses and Dissertations. 360.
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