SEPARATION OF 2(3),9(10),16(17),23(24)-TETRASUBSTITUTED PHTHALOCYANINES WITH NEWLY DEVELOPED HPLC PHASES

The synthesis of 2(3),9(10),16(17),23(24)-tetrasubstituted phthalocyan ines from 1,2-dicyano-4-alkoxybenzenes or the corresponding isoindolin es is reported, In each case, four isomers with D-2h, C-4h, C-2v and C -s symmetry are obtained in the statistical expected yield. The separa tion of the C-4h and the D-2h isomers was achieved successfully for th e first time from the other two isomers with newly developed HPLC phas es based on pi-pi interactions. In one case, phthalocyanine 12 could b e separated into the isomers 12a-d and characterized by UV/vis and H-1 -NMR spectroscopy. Due to line broadening at room temperature, T-1 and T-2 relaxation time measurements of two phthalocyanines (3 and 12) at different temperatures are carried out. Whether the broad peaks are d ue to aggregation or due to a short relaxation time is explained.