Synthesis and Characterization of5,10,15,20-Tetra[3-(3-trifluoromethyl)phenoxy] Porphyrin

Molecules

Cynthia P Tidwell¹  Prakash Bharara¹  Gretchen Rudeseal¹  Tiffany Rudeseal¹  Frank H Rudeseal¹  Christine A Simmer¹  Dugald McMillan¹  Katherine Lanier¹  L Dalila Fondren¹  LaTasha L Folmar¹ 

[1] ¹Department of Biology, Chemistry, and Mathematics, University of Montevallo, Station 6480 Montevallo, Alabama 35115, U.S.A. ²Department of Chemistry, University of Alabama, Box 870336 Tuscaloosa, Alabama 35487, U.S.A.

关键词: Porphyrin synthesis;    spectral properties;    cyclic voltammetry;    NMR.;   

DOI  :  10.3390/12071389

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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