Date of Award

Spring 4-29-2025

Degree Type

Thesis

Degree Name

MS Chemistry

Department

Chemistry and Biochemistry

Advisor

Alexander Fadeev, PhD

Committee Member

Sergiu Gorun, PhD

Committee Member

James Hanson, PhD

Keywords

phthalocyanine, organosilane, reflux, nucleophilic substitution, grafting, tetrahydrofuran

Abstract

This study began with the synthesis, purification, and catalytic application of hexadeca fluoro phthalocyanine zinc (F₁₆PcZn) derivatives functionalized with organosilane consuming thiol groups. The F₁₆PcZn was synthesized by reacting tetrafluorophthalonitrile (TFPN) with zinc acetate (Zn(OAc)₂) in 1-chloronaphthalene as a solvent, under a controlled heating process at 185°C for 90 minutes. The resulting blue solid was purified via vacuum filtration and recrystallization techniques to remove residual solvents and by-products, yielding pure F₁₆PcZn. The purity of the product was assessed through UV-Vis spectroscopy, MALDI analysis, and a molar extinction coefficient was determined.

Subsequent nucleophilic substitution of the fluorine atoms on F₁₆PcZn with organosilane compounds was successfully carried out, leading to the generation of organosilicon-functionalized F₁₆PcZn. Three new, distinct substituted organosilicon-functionalized products were synthesized using two distinct organosilanes and two distinct solvents. The first functionalized solution was the result of the nucleophilic substitution of F₁₆PcZn with (3-mercaptopropyl)trimethoxysilane using anhydrous sodium hydride (NaH) as a base via a five-day reflux using tetrahydrofuran (THF) as the solvent. The second distinct substituted organosilicon-functionalized solution came from the synthesis of F₁₆PcZn with (3-mercaptopropyl)methyl dimethoxysilane using NaH as a base via a five-day reflux with THF as the solvent.

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