The synthesis and characterization of zincphthalocyanines bearing functionalized bulky phenoxy substituents

The synthesis and characterization of zincphthalocyanine derivatives bearing functionalised bulky phenoxy substituents are described. Target precursors were prepared using a nucleophilic aromatic substitution reaction between 4,5-dichloropthalonitrile and 2,6-di-iso-propylphenol containing either H, Br, CN or NHCOCH3 at the p-position in an effort to tune both molecular and material properties. UV–vis and NMR analyses revealed that steric interactions between the bulky iso-propyl groups on adjacent phenoxy units effectively discouraged cofacial aggregation even in the solid state. This study explores the effectiveness of sterically hindered phenols situated at eight peripheral positions in improving some photo-physical properties.