Synthesis of Organosilicon Substituted FₓPcZn for the Preparation of Silica-Based Photo-Catalysts

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.