Synthesis of Octafluoroporphyrin |
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| Authors: | Chiranjeevulu Kashi Chu‐Chun Wu Dr Chi‐Lun Mai Prof Chen‐Yu Yeh Prof Chi K Chang |
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| Institution: | 1. Department of Chemistry, National Chung Hsing University, Taichung, Taiwan;2. Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan |
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| 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. |
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| Keywords: | electron-deficient compounds fluorine macrocycles porphyrinoids redox chemistry |
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