Synthesis of Tetraethyl ((2-Amino-1,4-Phenylene)Bis(Methylene)) Bis(Phosphonate): An Intermediate in the Synthesis of Amino-Substituted Conjugated Materials

Author

Ariel Ivan Torres Burgueno, The University of Texas Rio Grande Valley

Date of Award

12-2017

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Dr. Jose J. Gutierrez

Second Advisor

Dr. Evangelia Kotsikorou

Third Advisor

Dr. Jason Parsons

Abstract

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.

Comments

Copyright 2017 Ariel Ivan Torres Burgueño. All Rights Reserved.

https://www.proquest.com/dissertations-theses/synthesis-tetraethyl-2-amino-1-4-phenylene-bis/docview/2014469297/se-2?accountid=7119

Recommended Citation

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.
https://scholarworks.utrgv.edu/etd/360