ABAB-type Zn(II) phthalocyanines, crosswise-functionalized with two and four iodine atoms, respectively, have been efficiently prepared using statistical condensation procedures. Key to the selective preparation of the opposite ABAB isomers versus the adjacent AABB ones is the use of bulky 3,6-(3',5'-bis(trifluoromethyl)phenyl)phthalonitrile with hampered self-condensation capabilities.