New, Non-symmetrical 2:2 Phthalocyanines. 1,2,3,4,15,16,17,18-Octaphenyl-9,23(24)-dinitrophthalo- and 1,2,3,4,19,20,21,22-Octaphenyldiphthalo-11,29(30)-di-tert-butyl-dinaphthalocyanine Copper Complexes

The reaction between tetraphenylphthalonitrile and 4-phthalonitrile or 6-tert-butylnaphthalonitrile in the presence of copper(I) chloride gives a non-statistical mixture of non-symmetrical phthalocyanines from which 2:2 complexes are separated; in the reaction between substituted phthalo- and naphthalonitriles the 2:2 complex was a major product. The splitting of the Q-band in the electronic spectra depends on the differences in the electronic structure of the fragments of the non-symmetrical molecule.