Synthesis and spectral properties of novel metal-free and metallophthalocyanines bearing four 19-membered tetrathiadiaza macrocycles

Abstract

The synthesis of novel metal-free phthalocyanine 3 and metallophthalocyanines 4,5 and 6 containing four 19-membered tetrathiadiaza macrocycles at the peripheral positions are described for the first time. All new compounds were characterized by a combination of elemental analysis and H-1 NMR, C-13 NMR, IR, UV-Vis and MS spectral data. The metallophthalocyanines 4,5 and 6 have good solubility in organic solvents DMSO, DMF and THF. The aggregation behaviors of metal-free phthalocyanine 3 and metallophthalocyanines 4,5 and 6 were investigated at different concentrations in DMF and THF. All metallophthalocyanines were found to exist in monomeric form in DMF and THF at concentrations between 10 x 10(-6) and 2 x 10(-6) mol dm(-3). As the concentration increased to 5 x 10(-6) mol dm(-3), a deviation from ideality was observed due to the presence of aggregated species for all phthalocyanines. (C) 2013 Elsevier B.V. All rights reserved.