Synthesis, characterisation and aggregation properties of novel metal-free and metallophthalocyanines containing four 21-membered oxatetrathiadiaza macrocycles

The synthesis of novel metal-free phthalocyanine 4 and metallophthalocyanines 5, 6, 7 (MPcs, M - Ni, Zn, Co) containing four 21-membered oxatetrathiadiaza macrocycles at the peripheral positions was achieved by cyclotetramerisation of a novel 6,16-dioxo-5,6,7,9,10,12,13,15,16,17-decahydrotribenzo [h, k, n] [1,4,10,13,19,7,16]oxatetrathiadiazacyclohenicosine-24,25-dicarbonitrile. The aggregation behaviours of phthalocyanines 4, 5, 6 and 7 were investigated at different concentrations in dimethylformamide. No aggregation behaviour was observed in dimethylformamide at concentrations between 10 x 10(-6) and 1 x 10(-6) mol dm(-3). The aggregation properties of all phthalocyanines were also investigated in different solvents. All new compounds were characterised by a combination of elemental analysis and H-1 NMR, C-13 NMR, IR, UV-Vis and MS spectral data. (C) 2013 Elsevier B.V. All rights reserved.