SYNTHESIS, SEPARATION AND CHARACTERIZATION OF THE STRUCTURAL ISOMERS OF OCTA-TERT-BUTYLPHTHALOCYANINES AND DIENOPHILIC PHTHALOCYANINE DERIVATIVES

Octa-tert-butylphthalocyaninatonickel(II) (4) was synthesized from 3,5 -di-tert-butylphthalonitrile (1) and nickel acetate. A nonstatistical mixture of the four structural isomers 4 a-d was obtained. The isolati on of the structural isomers 4 a-d by preparative HPLC (MPLC) allowed their unequivocal identification and characterization by spectroscopic techniques. Moreover, a new family of tert-butyl-substituted phthaloc yanines 6-10 containing dienophilic functionalities were prepared by c ondensation of 3,5-di-tert-butylphthalonitrile (1) with 6,7-dicyano-1, 4-epoxy-1,4-dihydronaphthalene (5). The separation of the phthalocyani nes 6-10 and of some of their structural isomers was accomplished by n ormal column chromatography. The structural isomers were characterized by spectroscopic methods in terms of their symmetry.