Document Type

Honors Project

First Advisor

Dr. Ellen Mitchell

Degree Award Date

Spring 2001


Syntheses, Novel Metalloporphyrins


Analytical Chemistry | Chemistry


Three porphine structures including 5, 10, 15,20-tetraphenyl-21 H,23H-porphine (TPP) and two derivatives, 5, 10, 15,20-tetra(p-methylphenyl)-21 H,23H-porphine and 5, I O, 15 ,2 0-tetra(p-fl uoropheny 1 )-21 H,23 H-porphine, were synthesized and isolated using modified methods described by Adler. The three crystal products were characterized using 13 C NMR, 1 H NMR, infrared, and UV-Visible spectroscopies. Spectra obtained indicated successful synthesis of the three porphines. Insertion of zinc ion into tetraphenylporphyrin and the two porphine derivatives was attempted using a slightly modified method of Dorough. Comparison of the UV-vis spectra of the reaction mixture to metalloporphyrin spectra in the literature of Dorough and Rothemund provides evidence which suggests that the three metalloporphyrins, 5, I 0, 15,20- tetraphenylporphine zinc(II), 5, I 0, 15,20-tetra(p-methylphenyl)porphine zinc(II), and 5, 10, 15,20-tetra(p-fluorophenyl)porphine zinc(II) were successfully synthesized.