Synthesis of asymmetrically substituted fluorinated phthalocyanines

Unsymmetrical phthalocyanines (Pcs) have been an area of interest for various applications like photodynamic cancer therapy, photoconducting agents in photocopying devices, photocatalysis, optics and as catalysts. A number of different synthetic routes have been used in order to prepare asymmetrically substituted non-centrosymmetric Pcs, such as statistical mixed condensations, the use of specially designed phthalocyanine precursors, the use of polymer supports and the use of boron subphthalocynines as templates. All of these routes suffer from many experimental drawbacks that limit their universal applicability.;Meanwhile, it had been shown that nucleophilic substitution reactions on hexadecafluorophthalocyaninato zinc(II) with a variety of N,O,S and C nucleophiles led to polysubstituted phthalocyanines. In this work, mono substitution on hexadecafluorophthalocyaninato zinc(II) was the main interest. The main strategies that were followed to obtain novel mono substituted asymmetric pentadecafluorophthalocyaninato zinc(II) via solid phase organic synthesis, involved examples where the nucleophiles are attached to the polymer support.