SYNTHESIS AND CHARACTERIZATION OF TETRA(P-METHOXYPHENYL)PORPHYRIN USING SEQUENTIAL MICROWAVE-ASSISTED ORGANIC SYNTHESIS (S-MAOS) AND THE INSERTION Zn2+ ION INTO THE PORPHYRIN RING

• Main Author: NOVIANY (NIM : 20512039) ; Pembimbing Dr. Veinardi Suendo, Dr. Ciptati, DEWI
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/18294
• Institution: Institut Teknologi Bandung

Porphyrin and its derivatives are very interesting to be investigated due to their potential applications in several fields such solar cell, photodynamic therapy and photocatalysis. Tetra(p-methoxyphenyl)porphyrin (TMOPP) and zinc-tetra(p-methoxyphenyl)porphyrin (ZnTMOPP) are derivativates of porphyrin that were studied in this research. Both compounds had been successfully synthesized and characterized. The synthesis of TMOOP was carried out to the condensation reaction between pyrrole and p-methoxybenzaldehide under acidic conditions using solventless sequential microwave-assisted organic synthesis (S-MAOS) method with silica gel supporting phase. This method gives advantages compared to the conventional reflux method reported by Rothemund, Adler – Longo, and Lindsey, were it provides a faster reaction time. In addition, this method increases the yields up to 47 % compared to one-pot MAOS method. Preliminary analysis of TMOPP and ZnTMOPP were carried out by UV-Vis spectroscopy. UV-Vis spectra of TMOPP and ZnTMOPP show a maximum peak (Soret bands) at 422 and 422.5 nm, respectively, and also four weak peaks (Q bands) of TMOPP at 515, 556, 593, and 650 nm, and of ZnTMOPP at 555 and 569.5 nm. UV-Vis spectra of ZnTMOPP show a red shift compared to TMOPP. Emission peaks of TMOPP were observed at 659.5 and 723.89 nm, while of ZnTMOPP at 614 and 658 nm. Both emission peaks exhibit a blue shift from TMOPP to ZnTMOPP. UV-Vis and fluoresence spectra of each compound show a Stokes shift. TMOPP compound provide an infrared absoption peak at 3317 cm-1 that corresponds to the N-H asymmetric stretching vibration in the porphyrin ring. The absence of this absorption peaks in ZnTMOPP IR absorption spectrum proved that zinc metal ion has been succeeded to be introduced into porphyrin ring.