Date Thesis Awarded
Honors Thesis -- Open Access
Bachelors of Science (BS)
Elizabeth J. Harbron
This work presents the synthesis and photomodulation studies of Alkyne-functionalized poly(phenylene vinylene) (PPV) conjugated polymer nanoparticles and their subsequent functionalization with an azide-functionalized photochromic spirooxazine dye via a click reaction. A variation of the click reaction utilized in this project is the copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition. The synthesis and purification methods of spirooxazine are examined, and a general procedure for hydroxyspirooxazine condensation is established. The alkyne functionalization of 20% Br-functionalized PPV polymer is optimized. Alkyne-PPV nanoparticles are mixed with varying amounts of CuSO4 and sodium ascorbate to determine the conditions that cause nanoparticle aggregation. The procedure for removing aggregates and unreacted click reagents from the nanoparticle solution is established. Several click reactions were carried out to find the most optimal conditions for the click. Absorbance and fluorescence studies conducted on all click products showed a high degree of photomodulation. All click products exhibited significant quenching and almost full recovery without considerable photobleaching. These results suggest that we were able to successfully click spirooxazine dye to the PPV backbone and created a reversible photoswitch of the PPV fluorescence.
Lepekhina, Elena A., "Preparation of Spirooxazine-Functionalized Conjugated Polymer Nanoparticles by Click Chemistry" (2012). Undergraduate Honors Theses. William & Mary. Paper 555.
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