Synthesis and electrochemical properties of crown ether functionalized coumarin substituted cobalt and copper phthalocyanines

The synthesis of novel 6,7-[15-crown-5]-3-[p-(3,4-dicyanophenoxy)phenyl]coumarin (1)/6,7-[15-crown-5]-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin (2) and their peripherally/non-peripherally cobalt and copper phthalocyanine complexes (3–6) have been prepared and characterized by elementel analysis, 1H-NMR, MALDI-TOF, FT-IR and UV–Vis spectral data. Fluorescence intensity changes of compound 1 and 2 have been determined by addition of Na+ or K+ ions at 25 °C in THF. The effect of substitution type on the redox and aggregation behaviour of the compounds was investigated by voltammetry and in situ spectroelectrochemistry.