SYNTHESIS AND CHARACTERIZATION OF TETRAPHENYLPORPHYRIN AND ITS DERIVATIVE USING MICROWAVE-ASSISTED ORGANIC SYNTHESIS (MAOS)

• Main Author: MILANA ( NIM : 20510008); Pembimbing I : Dr. Ciptati, MS, M.Sc Pembimbing II : Dr. Veinardi S, PHUTRI
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/16821
• Institution: Institut Teknologi Bandung

Porphyrin is a heterocyclic macromolecular complex. Porphyrin compound has very wide applications such as photocatalyst, photodynamic agents for cancer therapy, photosensitizer in solar cell materials, active compound for solar water disinfection and solar water cleaning, and gas detector molecules. Various methods of porphyrin synthesis and their derivatives have been developed, but <br /> <br /> <br /> <br /> <br /> these methods use conventional heating that took a long time reaction and used harmful solvents or reagents. Therefore, a more efficient method is needed. Research of tetraphenylporphyrin synthesis and its derivatives were done by Microwave-Assisted Organic Synthesis (MAOS) method which use silica gel as support phase, silica acid and the mixture of 10% alumina/silica. <br /> <br /> <br /> <br /> <br /> Tetraphenylporphyrin synthesis carried out various reaction vessels, such as mortar, evaporating dish, petri dish, beaker, crucible, and teflon. The use of various reaction vessels was intended to examine the effectiveness of <br /> <br /> <br /> <br /> <br /> tetraphenylporphyrin synthesis reaction. The effectiveness of the tetraphenylporphyrin synthesis occurs when the reaction happened in mortar. One of porphyrin derivatives, tetra(p-methoxyphenyl)porphyrin, was synthesized by a <br /> <br /> <br /> <br /> <br /> hydrochloric acid (HCl)-silica and acetic acid-silica phase supports. The results of Tetraphenylporphyrin synthesis by acetic acid-silica phase support showed better results compared to hydrochloric acid (HCl)-silica. Synthesis of porphyrin derivatives from the mixture of p-methoxybenzaldehyde and benzaldehyde was intended to determine the easiness of two compounds form a porphyrin ring. Preliminary analysis of the synthesis results were done by thin layer chromatography (TLC), UV absorption spectroscopy, visible light, and followed by fluorescence analysis. From column chromatography measurement with the <br /> <br /> <br /> <br /> <br /> eluent n-hexane: ethyl acetate = 7: 1 (v / v), Rf values of tetraphenylporphyrin and tetra(p-methoxyphenyl)porphyrin compounds are 0.78 and 0.3, respectively. TLC test results of derived-porphyrin compounds from a mixture of pmethoxybenzaldehyde and benzaldehyde using eluent n-hexane: ethyl acetate (7:1) showed five stain compounds. The results of UV-visible spectra measurement in chloroform solvent showed tetraphenylporphyrin soret band at 417.9 nm and Q bands at 514.8; 548.1; 587.8 and 643.3 nm. The results of UV-visible spectrum measurements of tetra(p-methoxyphenyl)porphyrin showed shifted-light absorption to longer wavelengths (red shift), soret band at 421.6 nm and Q bands at 517.7; 555.2; 596.7; 649.2 nm. UV-Visible spectra of porphyrin derived compound, tetra(p-methoxyphenyl)porphyrin, showed maximum light absorption <br /> <br /> <br /> <br /> <br /> at different wavelengths from tetraphenylporphyrin that is 420.4 nm. <br /> <br /> <br /> <br /> <br /> Tetraphenylporphyrin emission spectra from reaction in various vessels showed an emission peak at the same wavelength that is 650 nm. Whereas an emission peak of tetra(p-methoxyphenyl)porphyrin showed 7 nm-shifts toward longer wavelengths compared to tetraphenylporphyrin. Structure determinations of synthesized-compounds are determined by infrared spectroscopy, Raman and Nuclear Magnetic Resonance (NMR). Tetraphenylporphyrin infrared absorption spectra showed absorption peaks at various wavenumbers, 2852 cm-1, 2920 cm-1, 2959 cm-1, 3022 cm-1, 3055 cm-1, 3317 cm-1 and 3348 cm-1. Raman shifts of <br /> <br /> <br /> <br /> <br /> Tetraphenylporphyrin crystal at 827 cm-1 and 1001 cm-1 showed pyrrole deformation ring and "pyrrole breathing", respectively. Proton NMR spectrum of Tetraphenylporphyrin showed peaks of pyrrole hydrogen singlet at 8.86 ppm <br /> <br /> <br /> <br /> <br /> chemical shift and ortho-phenyl hydrogen peak at 8.25 ppm chemical shift. The yield of Tetraphenylporphyrin synthesis using mortar container were 20%. Whereas, Tetraphenylporphyrin synthesis reaction in evaporating dish, petri dish vessels and 10% Alumina/silica phase-supported obtained 3%, 2% and 3,35%.