UTILIZATION OF PERFLUOROPHENYL-BODIPY AS FLUORESCENCE SENSOR MATERIAL FOR POLYCYCLIC AROMATIC HYDROCARBONS (PAHS) POLLUTANTS

• Main Author: Roro Hapsari, Niken
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/65433
• Institution: Institut Teknologi Bandung

Polycyclic Aromatic Hydrocarbons (PAHs) are types of organic pollutants that are mutagenic and carcinogenic and are found at low concentrations (ppb-ppm scale) in the environment. PAH detection technology using dyes material sensors is still in development stage. One of the promising PAH sensors is BODIPY (BF2-dipyrromethene) dyes. These materials can be easily fine-tuned to give a scaffold with certain characteristics and presence of specific interaction into PAH. Previously, the interaction between PAHs such as anthracene, naphthalene, and phenanthrene and BODIPYs is identified, via unusual weak H-type CH···F interaction between the axial CH proton of PAH and the F atom of BODIPY. The isosbestic point indicates good absorption and PAH forms a stable balance with BODIPY in the ground state. As fluorescence dye, perfluorophenyl-BODIPYs (PFP-BODIPYs) are known to have a high quantum yield value compared to other types. In this study, we aimed to synthesize and investigate the PFP-BODIPYs interaction with PAHs. The Hex-PFP-BODIPY was synthesized through three reaction steps, namely condensation of pyrrole with pentafluorobenzaldehyde under acidic conditions, followed by nucleophilic substitution on dipyrromethene, and complexation with BF3 to obtain a 33.7% yield of BODIPY. For comparison, pentafluorophenyl-BODIPY is also prepared. After purification by chromatography, the compounds were characterized by 1H-NMR. The interaction of PAH with PFP-BODIPY was evaluated by fluorescent colorimetry and UV-Vis. Pentafluorophenyl- BODIPY UV-Vis colorimetry with PAHs (anthracene, naphthalene, and phenanthrene) showed an isosbestic point at 220 300 nm for naphthalene and phenanthrene compared to 340 400 nm for anthracene. At the same concentration, the UV-Vis absorbance of naphthalene was lower than that of anthracene and phenanthrene. However, after the molar correction factor ( ) no isosbestic point is present, indicating very weak or no interaction between pentafluorophenyl-BODIPY and PAHs. Fluorescence titration of PFP-BODIPY and PAH showed a decreasing fluorescence intensity, while in Hex-PFP-BODIPY an increase of fluorescence is observed. This indicates that Hex-PFP-BODIPY interacts with PAHs.