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

Abstract

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 (H 2 PcH 16 ), as well as to the corresponding MPcH 16 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 (MPcF 16 ). Finally, we present a new and useful procedure for inserting a metal ion into a metal-free H 2 PcH 16 ring, by direct metalation, yielding the corresponding MPcH 16 complex. This last method is especially useful if you want to make different MPcH 16 complexes.