Effect of bromization on the properties of a series of sub-stituted 1,8,15,22-tetra(2,4-ditertbutylphenoxy) phthalocyanines

As a novel kind of functional dyes, phthalocyanines and metallophthalocyanines have been attracting the at-tention of many scientists for many years. Recently, the chemistry of Pcs has been undergoing a renaissance because Pcs and many of their derivatives exhibit theirproperties for potential application in materials science1,2 One of the main questions in the field of phthalocya-nines research is to modify the molecular structure re-placing the benzene-spherical hydrogen atoms by various s…

Effect of bromization on the properties of a series of substituted 1,8,15,22-tetra(2,4- ditertbutylphenoxy) phthalocyanines

A series of 1,8,15,22-tetra(2,4-ditertbutylphen- oxy) phthalocyanines a-(oAr)4PcM, M1=(H)2, M2=Pd, M3= Cu, M4=Zn, M5=Pb] were synthesized in this study. Each compound was bromized in two kinds of solvent. One is the solvent mixture of 1,1,2-trichloroethane and water, the other is 1,1,2-trichloroethane alone. The effects of solvent, bromine excess added and reaction duration on the bromization reac-tion were studied. The shift of maximum absorbance wave-length both in solution and in solid thin film was investigated comparatively, discovering that both were bathochromism but the former was more. TG data showed that the tem-perature of thermal decomposition decreased continuously with the increase of numbers of bromine. Finally, the frag-ments produced during the bromization of (OAr)4PcPb in 1,1,2- trichloroethane were characterized by GC/MS. Based on the electronic structure, the possible mechanism of de-composition of these compounds was presented and dis-cussed.