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The Synthesis and Subsequent Fluorescence Studies of Spirooxazine-Functionalized Poly(phenylene vinylene) Using the Gilch Polymerization Technique

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Author: Peth, Kathryn Anne
Advisor: Harbron, Elizabeth J.
Committee Members: Abelt, Christopher J.; Poutsma, John C.; Horvath, Robert
Issued Date: 2010-05-13
Subjects: FRET
URI: http://hdl.handle.net/10288/1984
Description: A synthetic route for and fluorescence study of spirooxazine-functionalized poly(phenylene vinylene) is presented. Attempts using the Heck polymerization have proven to be difficult; this fact combined with the lengthy synthetic route needed to simply make the monomers needed for polymerization along with discouraging fluorescence studies led to a search for a new synthetic route. This study shows the results of using the Gilch polymerization, which have proven to be successful for the creation of the poly(phenylene vinylene) backbone of the polymer. The monomers used for the polymerization were synthesized using a Williamson ether synthesis and electrophilic aromatic substution. Addition of the spirooxazine to the poly(phenylene vinylene) to form a spirooxazine-functionalized polymer (SO-PPV) via a SN2 reaction have also proven to be difficult, but a 100% and 25% functionalized SO-PPV product may have been obtained. Fluorescence and absorbance studies have been conducted on these products, and one particular study shows small but definite photomodulation that show a success in binding the SO group to the PPV polymer and thus obtaining the ability to selectively quench the fluorescence of the polymer.
Degree: Bachelors of Science in Chemistry

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