Formation of phthalocyanines deprotonated forms and their interaction with Zn Ions in the system 1,8-diazabicyclo[5.4.0]undec-7-ene-acetonitrile at 298 K

The formation of deprotonated forms of tetra(t-butyl)phthalocyanine ((H-2 tButPc) and octa(pentoxy)-phthalocyanine (H2OAmPc) in the system acetonitrile-1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at 298 K was studied by the method of spectrophotometric titration. With increasing DBU concentration sequential formation occurs of both mono- and douby deprotonated forms. The introduction of pentoxy groups into the fused benzene rings leads to a significant decrease in the acidity of the tetrapyrrole macrocycle compared with the tert-butyl substitution. The interaction of douby deprotonated forms of the phthalocyanines with zinc diacetate leads to the formation of metal complexes, the chelation constant of the latter is shown to correlate with the acidity of NH-protons in the nucleus of the macrocycle. For the chelation of more acidic tetra(t-butyl)-phthalocyanine an equimolar concentrations of zinc diacetate is sufficient, while the less acidic octa(pentoxy)-phthalocyanine requires almost 6-fold excess.