Phthalocyanines with Fluorinated Substituents

This section surveys synthesis of hexadecasubstituted phthalocyanines having at least one fluorine atom directly attached to each of four tetrasubstituted benzene rings. Among them one can distinguish (i) partly fluorinated hexadecasubstituted phthalocyanines [MPcF (R),(j J and two types of perfluorinated phthalocyanines -(ii) hexadecafluorophthalocyanines [MPcFig] and (iii) hexadecasubstituted phthalocyanines combining fluorine atoms and perfluorinated substituents [MPc(R/)i6]. The low synunetry phthalocyanines with only three perfluorinated isoindole units [MPc(R/)i2R] are also considered here. 

Various N-, 0-, S-, P- and C-nucleophiles can substitute fluorine atom(s) in TFPN and it can be therefore also used in the synthesis of the dinitrile precursors for hexadecasubstituted phthalocyanines bearing fluorine atoms along with other substituents. The nucleophilic substitution of fluorine atoms in TFPN occurs most easily in positions 4 and 5 and leads to 3,5,6-trifluoro- or 3,6-difluorophthalodini-triles, which can be used for synthesis of the corresponding a,a, p-dodeca- and a,a -octafluorinated phthalocyanines. 

Phthalocyanine analogues without fused benzene rings are usually named pophyrazines (PAs). Two types of fluorinated porphyrazines are known - the species with fluorine atoms attached directly in p-pyrrolic positions and compounds with fluorinated P-substituents. 

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