Octa- and tetra-(benzo-15-crown-5)phthalocyanines in surfactant-containing solutions

Abstract

The behavior of octa-(benzo-15-crown-5)phthalocyanine (H2cr8Pc), as well as cobalt octa- and tetra-(benzo-15-crown-5)phthalocyaninates (Cocr8Pc and Cocr4Pc), in aqueous solutions containing cationic or anionic surfactants, such as cetyl trimethylammonium bromide (CTAB), sodium carboxymethyl cellulose (Na-CMC), and sodium dodecyl sulfate (SDS), is studied using electronic spectroscopy. The presence of eight benzo-15-crown-5 ether fragments on the periphery of the phthalocyanine ring is shown to facilitate the dissolution of Pc in an aqueous environment. The interactions between CTAB and crown-containing Pc promotes the dissolution of H2cr8Pc; Cocr8Pc; and, to a lesser degree, Cocr4Pc, which is accompanied by the appearance of molecular aggregates, including heteronuclear cofacial dimers. The presence of a metal in the ring is not the necessary condition of the process. In microscopically heterogeneous medium, such as an aqueous SDS-containing solution, H2cr8Pc is present in monomeric form at SDS concentrations close to C cr and in dimeric form at SDS content below C cr. Under similar conditions (environment, surfactant), Cocr4Pc can exist in monomeric form at SDS concentrations much high than C cr. The effect of the size of cation on the form of the crown-containing Pc in an aqueous solution is illustrated by an example of H2cr8Pc. Na-CMC promotes the dissolution of Pc and enables one to produce K+/Mcr8Pc-modified films from aqueous solutions.