Novel Ball-Type Phthalocyanines with Eight Benzotriazole Groups: Synthesis, Computational DFT Studies, and Supercapacitor Properties

Novel four MBTOB-bridged ball-type metallophthalocyanines were obtained from 4,4'-((methylenebis(6-(2H-benzo[d][1, 2, 3]triazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)-2, 1-phenylene))bis(oxy))diphthalonitrile by means of transition metal (II) acetate salts in 2-dimethylaminoethanol. The new starting bisphthalonitrile compound was accomplished from 2,2'-methylenebis[6-(benzotriazol-2-yl)-4-tert-octylphenol] and 4-nitrophthalonitrile in dimethylformamide under the catalysis of potassium carbonate at 50 degrees C. The structural characterization of the compounds was accomplished by infrared, proton-nuclear magnetic resonance, matrix-assisted laser desorption/ionisation time-of-flight mass, and ultraviolet-visible spectroscopic methods. The supercapacitor performances of the electrodes were examined by cyclic voltammetry, galvanostatic charge discharge, and electrochemical impedance spectroscopy analyses. The specific capacitances obtained from the GCD measurements were calculated as 320.4 +/- 15.1 F g(-1) for ball-type zinc (II) phthalocyanine in three electrode systems. The highest specific capacitance value was found in the electrode containing ball-type nickel (II) phthalocyanine as 929.8 +/- 32.8 F g(-1) at a scan rate of 100 mV s(-1). In symmetric supercapacitor measurements, the capacitance retention value was 100.7% after 5000 cycles.