The syntheses of amphiphilic antimony(V)-phthalocyanines and spectral investigation on their aggregation behaviors in aqueous and non-aqueous solutions.

Abstract Three amphiphilic antimony(V)-phthalocyanines have been synthesized by treating [Sb(R 4 Pc)(OH) 2 ] + salts in concentrated H 2 SO 4 and isolated as zwitter ions, [Sb(R 4 Pc)(SO 4 H)(SO 4 )], where R 4 Pc denotes tetra-substituted phthalocyaninate; R 4 Pc = pc (R = H), tbpc (R =  t Bu), and tObpc (R = O n Bu). Their solubility (R = tbpc > pc > > tObpc in H 2 O (much improved by the presence of surfactant or alcohol) while tbpc > tObpc > > pc in CH 2 Cl 2 ) and aggregation behaviors are highly sensitive to the nature of the peripheral substituents. The pc and tbpc derivatives form well-behaved J-aggregates in aqueous media in the presence of surfactant or alcohol.