Dimer Formation of a Phthalocyanine and its Iron Complex in Solid State and in Solution

Iron phthalocyanine derivatives with eight carbazole substituents were synthesized and the axial ligands were removed leading to paramagnetic (S=1), four coordinate ferrous complexes. Depending on the position of additional t-butyl groups, these phthalocyanines form dimers in solution and in the solid state. A dimeric iron-phthalocyanine was isolated and analysed by paramagnetic NMR and by single-crystal X-ray diffraction. The dimers are hold together by pi-pi interaction between 16 carbazole units and by a Fe-Fe interaction. The dimers are stable in solution up to at least 340K.