A simple synthesis of symmetric phthalocyanines and their respective perfluoro and transition-metal complexes

We report a simple synthesis protocol for making phthalocyanines (Pcs) starting from phthalonitriles. This method is general and requires no specialised equipment. The complexes are isolated and characterised using X‐ray diffraction, NMR, FTIR and Raman spectroscopy and high‐resolution mass spectrometry. First, we study and present a one‐step synthesis route to a metal‐free Pc (H₂PcH₁₆), as well as to the corresponding MPcH₁₆ complexes of Mn, Fe, Co, Ni, Cu and Zn. Then, we show that this route can also be used to make the fluorinated Pc analogues (MPcF₁₆). Finally, we present a new and useful procedure for inserting a metal ion into a metal‐free H₂PcH₁₆ ring, by direct metalation, yielding the corresponding MPcH₁₆ complex. This last method is especially useful if you want to make different MPcH₁₆ complexes.