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Synthesis of Octafluoroporphyrin
Author(s) -
Kashi Chiranjeevulu,
Wu ChuChun,
Mai ChiLun,
Yeh ChenYu,
Chang Chi K.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201511702
Subject(s) - hypsochromic shift , chemistry , porphyrin , molecule , ring (chemistry) , yield (engineering) , magnesium , solid state , condensation , photochemistry , medicinal chemistry , organic chemistry , materials science , fluorescence , physics , quantum mechanics , metallurgy , thermodynamics
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.