title: Synthesis of Octafluoroporphyrin.
abstract: Despite the long list of known fluoroporphyrinoids, the most fundamental 2,3,7,8,12,13,17,18-octafluoroporphyrin (OFP) has not been synthesized until now. It is achieved by condensation of two molecules of tetrafluoro-dipyrrylmethane-2-carboxaldehyde in the presence of magnesium(II) salts. The fluorinated dipyrrylmethane also gives 5,15-bis(pentafluorophenyl)-OFP (F18P) with a reasonable yield. Both Mg/OFP and Zn/F18P in the solid-state reveal an essentially flat structure. The fluoro groups impart as much as a 0.5 V anodic shift for porphyrin ring oxidation/reduction, as well as hypsochromic shifts in the Uv-vis spectra.
authors.affiliation: Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan.
authors.forename: Chiranjeevulu
authors.initials: C
authors.lastname: Kashi
authors.affiliation: Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan.
authors.forename: Chu-Chun
authors.initials: CC
authors.lastname: Wu
authors.affiliation: Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan.
authors.forename: Chi-Lun
authors.initials: CL
authors.lastname: Mai
authors.affiliation: Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan. cyyeh@dragon.nchu.edu.tw.
authors.forename: Chen-Yu
authors.initials: CY
authors.lastname: Yeh
authors.affiliation: Institute of Chemistry, Academia Sinica, Nankang, Taipei, 115, Taiwan. changc@msu.edu.
authors.forename: Chi K
authors.identifier: http://orcid.org/0000-0002-4113-1950
authors.initials: CK
authors.lastname: Chang
keywords: electron-deficient compounds; fluorine; macrocycles; porphyrinoids; redox chemistry