Synthesis of Octafluoroporphyrin

Chiranjeevulu Kashi; Chu-Chun Wu; Chi-Lun Mai; Chen-Yu Yeh; Chi K Chang

doi:10.1002/anie.201511702

Synthesis of Octafluoroporphyrin

Angew Chem Int Ed Engl. 2016 Apr 11;55(16):5035-9. doi: 10.1002/anie.201511702. Epub 2016 Mar 16.

Authors

Chiranjeevulu Kashi¹, Chu-Chun Wu¹, Chi-Lun Mai¹, Chen-Yu Yeh², Chi K Chang³

Affiliations

¹ Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan.
² Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan. cyyeh@dragon.nchu.edu.tw.
³ Institute of Chemistry, Academia Sinica, Nankang, Taipei, 115, Taiwan. changc@msu.edu.

PMID: 26991696
DOI: 10.1002/anie.201511702

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.

Keywords: electron-deficient compounds; fluorine; macrocycles; porphyrinoids; redox chemistry.

Publication types

Research Support, Non-U.S. Gov't