Porphyrin polyfluorinated

Cesium fluoroxysulfate reacts with derivatives ot porphyrin to give i-fluoro-porphynns accompanied by polyfluorinated products [35, 36]... 

More recently, Ellis and Lyons have reported1,1 that polyfluorinated iron(III)porphyrin complexes are stable, highly active oxidation catalysts that catalyze the unprecedented selective hydroxylation of isobutane with molecular oxygen at ambient temperature. 

Condensation of pyrroles with carbonyl compounds under Lewis acid catalysis followed by oxidation provides an efficient route to the porphyrin ring system. This has been effectively used to prepare polyfluorinated porphyrins from 3-fluoro and 3,4-difluoropyrroles, as well as pyrroles substituted with fluorinated side chains in these positions. For example, DiMagno and coworkers extended their studies of highly electron-deficient porphyrins to a series of 2,3,7,8,12,13,17,18-octafluoro-5,10,15,20-tetraarylporphyrins 96, including the perfluorinated compound, by BFs-catalyzed condensation of 3,4-difiuoropyrrole with benzaldehydes followed by dichloro dicyano quinone (DDQ) oxidation (Fig. 3.46). A similar approach was used by Leroy and coworkers. ... 

As can be seen from the brief overview in this section, fluorinated pyrroles have played a major role in the development of new tools for the study of porphyrin chemistry. The high electronegativity of fluorine, especially in polyfluorinated analogues, has been particularly useful to alter properties and also to study the electronic effects in porphyrin structure and function. 

De Medeiros MAC, Gorgy K, Deronzier A, Cosnier S (2008) Design of new electropolymerized polypyrrole films of polyfluorinated Zn(II) and Mn(III) porphyrins towards electrochemical sensors. Mater Sci Eng C Biomim Supramol Syst 21 731-738... 

L. A. Lucia, T. Yui. R. Sasai, S. Takagi, K. Takagi, H. Yoshida, D. G. Whitten, H. Inoue, Enhanced aggtegationbehavior of antimony(V) porphyrins in polyfluorinated surfactant/clay hybrid nticroenvironment, J. Phys. Chem. B 107, 3789-3797 (2003). 

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