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 DiMagno

Research output: Contribution to journalArticle

96 Citations (Scopus)

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 - Jan 1 1997

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Zinc
Bearings (structural)
Ligands
Oxidation
Electrons
Porphyrins
Invariance
Conformations
5,10,15,20-tetraphenylporphyrin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "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",
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.",
author = "Woller, {Eric K.} and Stephen DiMagno",
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T1 - 2,3,7,8,12,13,17,18-Octafluoro-5,10,15,20-tetraarylporphyrins and Their Zinc Complexes

T2 - First Spectroscopic, Electrochemical, and Structural Characterization of a Perfluorinated Tetraarylmetalloporphyrin

AU - Woller, Eric K.

AU - DiMagno, Stephen

PY - 1997/1/1

Y1 - 1997/1/1

N2 - 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.

AB - 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.

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