Chemistry and Physics Faculty Proceedings, Presentations, Speeches, Lectures

Event Name/Location

2022 Undergraduate Student Symposium / Nova Southeastern University

Event Name

2022 Undergraduate Student Symposium

Event Location

Fort Lauderdale, Florida / Nova Southeastern University

Document Type


Publication Date

Spring 4-7-2022


The purpose of this study was to determine the effects of fluorinated substitution of meso phenyl porphyrins on porphyrin basicity. The protonation of meso-Tetra(2,3,4-trifluoromethylphenyl) porphyrin (TF) and meso-Tetra(pentafluorophenyl) porphyrin (PF) will be studied through UV vis spectroscopy. Protonation is achieved by titration of each porphyrin in toluene with trifluoroacetic acid (TFA). The presence of a wavelength shift from the free base Soret to the protonated Soret will indicate the formation of a dication. The data from the UV spectra will be used to calculate the pKa values associated with each porphyrin. Based on the results, the average pKa for TF upon protonation was 2.07, while the average pKa for PF was 1.36 over four trials. A greater acidic value for PF was indicated from these results. In addition, a significant increase in the amount of acid added was noted during the protonation of PF when compared to the amount of acid needed for TF. This could indicate a correlation between the fluorinated position in the porphyrin and the formation of dication.