title: Synthesis and characterization of 5,10,15,20-tetra[3-(3-trifluoromethyl)phenoxy] porphyrin.
abstract: The newly synthesized 5,10,15,20-tetra[3-(3-trifluoromethyl)phenoxy]porphyrin, TTFMPP, has been characterized using mass spectroscopy, 1H-, 13C- and 19F-NMR, MALDI-TOF mass spectrometry, UV-Vis and fluorescence spectrophotometry, and cyclic voltammetry. The NMR confirmed the structure of the compound and the mass spectrum was in agreement with the proposed molecular formula. The UV-Vis absorption spectrum of TTFMPP shows characteristic spectral patterns similar to those of tetraphenyl porphryin, with a Soret band at 419 nm and four Q bands at 515, 550, 590, and 648 nm. Protonation of the porphyrin with TFA resulted in the expected red shift of the Soret band. Excitation at 419 nm gave an emission at 650 nm. The quantum yield of the porphyrin was determined to be 0.08. Cyclic voltammetry was used to determine the oxidation and reduction potentials of the new porphyrin. Two quasi-reversible one-electron reductions at -1.00 and -1.32 V and a quasi-reversible oxidation at 1.20 V versus the silver/silver chloride reference electrode with tetrabutylammonium tetrafluoroborate as the supporting electrolyte in methylene chloride were observed.
authors.affiliation: Department of Biology, Chemistry, and Mathematics, University of Montevallo, Station 6480 Montevallo, Alabama 35115, USA. tidwellc@montevallo.edu
authors.forename: Cynthia P
authors.initials: CP
authors.lastname: Tidwell
authors.forename: Prakash
authors.initials: P
authors.lastname: Bharara
authors.forename: Gretchen
authors.initials: G
authors.lastname: Rudeseal
authors.forename: Tiffany
authors.initials: T
authors.lastname: Rudeseal
authors.forename: Frank H
authors.initials: FH
authors.lastname: Rudeseal
authors.forename: Christine A
authors.initials: CA
authors.lastname: Simmer
authors.forename: Dugald
authors.initials: D
authors.lastname: McMillan
authors.forename: Katherine
authors.initials: K
authors.lastname: Lanier
authors.forename: L Dalila
authors.initials: LD
authors.lastname: Fondren
authors.forename: LaTasha L
authors.initials: LL
authors.lastname: Folmar
authors.forename: Ken
authors.initials: K
authors.lastname: Belmore
mesh_terms: D002725:Chloroform; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*; D011522:Protons
chemical_list: C523804:5,10,15,20-tetra(3-(3-trifluoromethyl)phenoxy)porphyrin; D011166:Porphyrins; D011522:Protons; D002725:Chloroform