Syntheses and properties of amphiphilic zinc(II), nickel(II), and palladium(II) phthalocyanines with eight tri(oxyethylene) chains introduced at non-peripheral α positions

Abstract

Amphiphilic zinc(II) (1), nickel(II) (2), and palladium(II) (3) complexes of 1,4,8,11,15,18,22,25-octakis(1,4,7,10-tetraoxaundecyl)phthalocyanine were synthesized and characterized by elemental analysis and MALDI-TOF mass and 1H NMR spectroscopies. Electronic absorption spectra showed aggregation of the phthalocyanine molecules in [Formula: see text]O for 2 and 3, while the monomeric form for 1 in [Formula: see text]O, and 1, 2, and 3 in [Formula: see text]. The cyclic voltammograms of 1, 2, and 3 in [Formula: see text] showed that oxidation of the phthalocyanine ring occurs easily in these complexes. This may be due to the energetically increased HOMO, coming from the deformation of the phthalocyanine ring. Steric hindrance between the [Formula: see text]-introduced 1,4,7,10-tetraoxaundecyl groups (tri(oxyethylene) chains) within the phthalocyanine molecule gives rise to the deformation of the phthalocyanine ring, which decreases the aggregating nature of the present complexes.