SYNTHESIS OF PHTHALOCYANINES WITH ONE SULFONIC-ACID, CARBOXYLIC-ACID,OR AMINO GROUP

Monofunctional phthalocyanines 7a,b, one bearing a sulfo and the other one a carboxyl group, were synthesized by lithium alkoxyde-catalyzed statistical tetramerization of 4-(4-tert-butylphenoxy)-1,2-benzenedica rbonile (3c) with 1,2-dicyanobenzenes 3a,b carrying a carboxyl or sulf o group. Tribenzonaphthoporphyrazines 9a,b with one carboxyl or amino group were prepared under similar reaction conditions by tetramerizati on of 3,6-dihexyloxy-1,2-benzenedicarbonitrile with 6-amino- or 6-carb oxy-2,3-naphthalenedicarbonitrile 6b,6a. The zinc(II)-containing macro cycles 7a, b, 9a, b obtained in yields of 11-20% were purified by colu mn chromatography and characterized by UV/Vis, mass, and H-1-NMR spect roscopy.