Position Isomers Constituting Cu-Phthalocyanine-N-Isologue and Its Separation

Abstract

Cu-Bz-azaphthalocyanine (Cu-Bz-AzaPC) synthesized from mixed raw materials of phthalic anhydride and quinolinic acid 1 : 1 mole ratio was separated to several colour components by the newly developed sulfuric acid soluble method. In this result, it was separable to pyridine ring numbers containing in Cu-Bz-AzaPC. Cu-tetrapyridinoporphyrazine (Cu-TPP) was separated with 20. 00 wt% sulfuric aqueous solution. And increasing with sulfuric acid concentration, Cu-phthalocyanine-N-isologue having each pyridine rings was separated as follows ; having three pyridine rings was separated with 35. 00 wt%, having two pyridine rings was separated with 64. 47 wt% and having one pyridine ring was separated with 73. 13 wt%, respectively. Above results were confirmed from nitrogen contents from elemental analysis and comparison of IR spectra of its separate with relative colouring matters such as Cu-Bz-AzaPC synthesized from mixed raw materials of various mole ratio.
Examining details of the IR spectra for 12 fractions of Cu-PC-N-isologue having two pyridine rings, si. e., Cu-dibenzodipyridinoporphyradine which was separated from Cu-Bz-AzaPC with 64. 47 wt% ulfuric aqueous solution, the shift of the absorption maximum at the range of 800 cm^-1 to 700 cm^-1due to the C-H streching vibration in the 1, 2-disubstituted benzene or 2, 3-disubstituted pyridine were observed.
These phenomena were inferred that 4 or 5 position isomers yielded from the difference of bonding position of pyridine ring and/or the difference of condensation situation of pyridine ring at the synthesis state of Cu-dibenzodipyridinoporphyrazine.