Chemoselective Synthesis of Aryloxy-Substituted Phthalocyanines

The synthesis of
the first examples of 8-fold α-aryloxy-substituted
phthalocyanines is described. 3,6-Diiodophthalonitrile was used as
a precursor for a series of 3,6-aryloxy-substituted phthalonitriles,
and a lead-mediated macrocyclization was employed to afford the corresponding
free-base phthalocyanine complexes. The optical, electrochemical,
and aggregation properties of these complexes can be tuned by varying
the substituents on the aryloxy groups or by changing the pH value.