The synthesis of di-disubstituted phthalocyanines

The purpose of this work was to devise an efficient synthetic route to di-disubstituted phthalocyanines. No preparatory method for this type of phthalocyanine currently exists. This type of phthalocyanine is of potential use as a monomer in the non-cross linked polymerization of phthalocyanine into a processable material. Three approaches to the synthesis of this compound were investigated; direct mixing of equal amounts of two different precursors, use of a metal ligand complex to hold two precursors in position while two different precursors are added, and the use of two compounds that can form a phthalocyanine only by joining alternately.; The first two approaches were not successful, however the last method was explored extensively and did produce both hydrogen phthalocyanines and metallo phthalocyanines. The physical and spectral properties of these compounds are discussed. The metallo di-disubstituted phthalocyanines synthesized are the first examples of metallo phthalocyanines having a visible spectra which exhibits four Q band absorptions. Unsubstituted or symmetrically substituted metallo phthalocyanines show only two Q bands. This unusual effect by the di-disubstituted metallo phthalocyanines is due to the change in symmetry from the normal D{dollar}sb{lcub}rm 4h{rcub}{dollar} type to D{dollar}sb{lcub}rm 2h{rcub}{dollar}.