Synthesis of an NLO Active Organic Molecule

Nikash Patel

Date of Award

2008

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Scudder, Paul

Keywords

Nonlinear Optical, Organic Synthesis, Second Harmonic Generation

Area of Concentration

Chemistry

Abstract

The synthesis of an organic molecule, 4-(4�-cyanophenylazo) phenoxyundecanoyl chloride, with possible NLO active properties was completed. The molecule followed the D-n-A configuration, which included an azobenzene chromophore as the conjugate n bridge. There were three intermediate steps in the synthetic scheme including the formation of the cyano dye itself. Different variations were explored in order to obtain a decent product yield on all steps. In order to attach the long alkyl chain of 11-bromoundecanoic acid to the azo dye, it was necessary to protect the COOH of 11-bromoundecanoic acid by initially forming a methyl ester. Once the azo dye had been attached, the remaining reactions involving the formation of a carboxylic acid and an acid chloride were facile. All products and intermediates were verified using 1H NMR, 13C NMR, and IR spectroscopy. An overall yield of 9% was recorded. The final product was sent to Pomona College to be made into multilayer thin films using the polyelectrolyte layer-by-layer chemisorption.

Rights

This bibliographic record is available under the Creative Commons CC0 public domain dedication. The New College of Florida, as creator of this bibliographic record, has waived all rights to it worldwide under copyright law, including all related and neighboring rights, to the extent allowed by law.

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