Next Article in Journal
Atmospheric Pressure Microwave Assisted Heterogeneous Catalytic Reactions
Next Article in Special Issue
New “Green” Approaches to the Synthesis of Pyrazole Derivatives
Previous Article in Journal
Comparison of the Biological Properties of Several Marine Sponge-Derived Sesquiterpenoid Quinones
Previous Article in Special Issue
Facile Synthesis of Optically Active Imidazole Derivatives
Molecules 2007, 12(7), 1389-1398; doi:10.3390/12071389

Synthesis and Characterization of 5,10,15,20-Tetra[3-(3-trifluoromethyl)phenoxy] Porphyrin

1,* , 1
1, 1, Jr 1, 1, 1, 1, 1, 1 and 2
1 Department of Biology, Chemistry, and Mathematics, University of Montevallo, Station 6480 Montevallo, Alabama 35115, U.S.A. 2 Department of Chemistry, University of Alabama, Box 870336 Tuscaloosa, Alabama 35487, U.S.A.
* Author to whom correspondence should be addressed.
Received: 30 May 2007 / Revised: 8 July 2007 / Accepted: 9 July 2007 / Published: 11 July 2007
(This article belongs to the Special Issue Heterocycles)
Download PDF [80 KB, uploaded 18 June 2014]


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, andcyclic voltammetry. The NMR confirmed the structure of the compound and the massspectrum was in agreement with the proposed molecular formula. The UV-Vis absorptionspectrum of TTFMPP shows characteristic spectral patterns similar to those of tetraphenylporphryin, 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 wasdetermined to be 0.08. Cyclic voltammetry was used to determine the oxidation andreduction 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/silverchloride reference electrode with tetrabutylammonium tetrafluoroborate as the supportingelectrolyte in methylene chloride were observed.
Keywords: Porphyrin synthesis;spectral properties;cyclic voltammetry;NMR. Porphyrin synthesis; spectral properties; cyclic voltammetry; NMR.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
MDPI and ACS Style

Tidwell, C.P.; Bharara, P.; Rudeseal, G.; Rudeseal, T.; Rudeseal, F.H., Jr; Simmer, C.A.; McMillan, D.; Lanier, K.; Fondren, L.D.; Folmar, L.L.; Belmore, K. Synthesis and Characterization of 5,10,15,20-Tetra[3-(3-trifluoromethyl)phenoxy] Porphyrin. Molecules 2007, 12, 1389-1398.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert