2,3,7,8,12,13,17,18-Octafluoro-5,10,15,20-tetraarylporphyrins and Their Zinc Complexes: First Spectroscopic, Electrochemical, and Structural Characterization of a Perfluorinated Tetraarylmetalloporphyrin

Eric K. Woller, Stephen G. DiMagno

Research output: Contribution to journalArticle

96 Scopus citations

Abstract

We report a convenient and general synthesis of β-octafluoroporphyrins bearing meso-tetraaryl substituents, including the first synthesis and full characterization of a perfluorinated tetraarylporphyrin, perfluoro-5,10,15,20-tetraphenylporphyrin, 2. The structural, spectroscopic, and electrochemical data indicate that β-octafluoro-meso-tetraarylporphyrins are a new class of planar, electron-deficient ligands. Particularly impressive is the 0.5 V window over which the formal oxidation potential can be tuned using only aryl substituents. The invariance of the ligand structure with increasingly positive formal oxidation potential is a key advance; electronic effects have been severed from the nonplanar conformations exhibited by all other highly electron-deficient porphyrins.

Original languageEnglish (US)
Pages (from-to)1588-1593
Number of pages6
JournalJournal of Organic Chemistry
Volume62
Issue number6
DOIs
StatePublished - 1997

ASJC Scopus subject areas

  • Organic Chemistry

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