Synthesis and characterization of partially β-fluorinated 5,10,15,20-tetraphenylporphyrins and some derivatives

The synthesis of partially β-fluorinated meso-tetraphenylporphyrins using Lindsey conditions, has been examined, starting either from 3,4-difluoro-1 H-pyrrole or from 3-fluoro-1 H-pyrrole. In the case of the first synthon, condensation with pyrrole and benzaldehyde afforded a mixture of porphyrins o...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 58; no. 33; pp. 6713 - 6722
Main Authors Leroy, Jacques, Porhiel, Emmanuel, Bondon, Arnaud
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 12.08.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
electronic spectra
fluorinated porphyrins
fluorinated pyrroles
Physical Sciences
protecting groups
Science & Technology
protecting groups
electronic spectra
fluorinated porphyrins
fluorinated pyrroles
PYRROLE
ELECTRONIC-SPECTRA
PORPHYRINS
COMPLEXES
FLUOROPYRROLES
Online AccessGet full text

Cover

More Information
Summary:The synthesis of partially β-fluorinated meso-tetraphenylporphyrins using Lindsey conditions, has been examined, starting either from 3,4-difluoro-1 H-pyrrole or from 3-fluoro-1 H-pyrrole. In the case of the first synthon, condensation with pyrrole and benzaldehyde afforded a mixture of porphyrins of general formula β-F n TPP ( n=0,2,4,6,8) displaying linearly correlated spectroscopic and electrochemical properties. With the second synthon, condensation with benzaldehyde produced an unresolvable mixture of β-tetrafluoroporphyrins presenting spectroscopic and electrochemical properties in coherence with those observed in the first case. Preliminarily, the synthesis and isolation of the hitherto unknown 3-fluoro-1 H-pyrrole has been approached via several methods. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00677-4