Fibrous assemblies made of amphiphilic metallophthalocyanines

A family of copper and zinc phthalocyanine-based amphiphililes possessing r acemic and optically active diol units, (rac)-ZnPc(OH)(16), (rac)-CuPc(OH)( 16), and (S)-CuPc(OH)(16), have been synthesized. The self-assembling prope rties of these amphiphiles in aqueous solution have been studied by W-vis, Fourier transform infrared (FTIR) and circular dichroism (CD) spectroscopie s, X-ray diffraction (XRD) patterns, and transmission electron microscopy ( TEM). Only the copper complexes produced fibrous assemblies from aqueous so lutions through two noncovalent bondings: pi-pi interaction among phthalocy anine rings and hydrogen bonds among diol units. The formation of fibrous a ssemblies strongly depends on the central metal of the phthalocyanine compl ex. The optically active (S)-CuPc(OH)(16) is stacked and arranged in a left -handed helix. The chirality of diol units in (S)-CuPc(OK)(16) also affects the intercolumnar lattice of phthalocyanine stacks.