Fluorinated Porphyrazines

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. 

---

Abstract This chapter describes the synthesis of phthalocyanines, subphthalocyanines and porphyrazines bearing fluorine atoms and/or perfluorinated alkyl or aryl groups. Influence of fluorination of macrocycle on its physico-chemical properties and perspectives of application is also briefly considered. 

Tetrafluoroporphyrazine H2PAF4 (149) bearing one fluorine atom in each of four pyrrole rings (Scheme 38) can be prepared as a regioisomeric mixture from unsubstituted porphyrazine H2PA (147) in a two-stage procedure. 

Porphyrazines combining fluorinated aryl groups with cyano group in each pyrrole ring can be conveniently prepared [91] starting from malonodinitrile and fluorinated benzaldehydes 163a,b (Scheme 41). 

Altunkaya M, Gonca E (2011) Synthesis and characterization of new soluble fluorinated seco-porphyrazines. Polyhedron 30 1035-1039... 

---