Synthesis and characterization of novel HMPM bridged ball-type metallophthalocyanines, and their DFT studies and electrochemical performance as supercapacitor electrodes

Abstract

Novel 4, 4′-((((2-(3, 4-dicyanophenoxy)-5-methyl-1, 3-phenylene) bis (methylene)) bis (4-methyl-3, 1-phenylene)) bis (oxy)) -bridged ball-type phthalocyanines were achieved from 4, 4′-((((2-(3, 4-dicyanophenoxy)-5-methyl-1, 3-phenylene) bis (methylene)) bis (4-methyl-3, 1-phenylene)) bis (oxy)) diphthalonitrile through appropriate transition metal (II) acetate salts in 2-dimethylaminoethanol. The new tris-phthalonitrile precursor was achieved from 3,3′-((2-hydroxy-5-methyl-1,3-phenylene) bis (methylene)) bis (4-methylphenol), and 4-nitrophthalonitrile with the presence of catalyst potassium carbonate in dimethylformamide at 50○C. The structural verification of the compounds was accomplished by proton-nuclear magnetic resonance, matrix-assisted laser desorption/ionization time-of-flight mass, infrared, and ultraviolet–visible spectroscopic methods.The BTCuPc electrode material exhibited a specific capacitance of 265 F.g−1 at a scan rate of 5 mV.s−1 in 3.0 M KCl aqueous electrolyte. In addition, a wide operating potential range (1.5 V) was achieved in the aqueous electrolyte.