Behavior of octa(benzo-15-crown-5)- and tetrasulfophthalocyanines in the presence of water-soluble C60 compounds

Abstract

Octa[(4′-benzo-15-crown-5)oxy]phthalocyanine was shown to dissolve in the presence of water-soluble fullerene compounds C60Cl(NHCH2CH2NH3+)5(−OOCCF3)5 or C60Cl(C6H4CH2CH2COONa)5. The solubilization of phthalocyanine was attributed to the possibility of formation of the hydrogen bonds N-H...O(CH2) and coordination of the sodium cations inside the cavities of the crown ether fragments for the cationic and anionic fullerene derivatives, respectively. Solubilization of the crown-containing phthalocyanine with participation of water-soluble fullerene compounds proceeded with the formation of aggregated forms. A monomeric form of nickel tetrasulfonated phthalocyaninate in the presence of an equimolar amount of C60Cl(NHCH2CH2NH3+)5(−OOCCF3)5 in 50% ethanol is transformed into a dimeric form. The structures of the fullerene-containing compounds and their state in solution facilitate the stacking aggregation of phthalocyanines.