Supramolecular Self-Assembly Properties of Metallo-Ionic Phthalocyanines Constituting Regioisomers

Abstract

We describe the synthesis and properties of metallo-ionic phthalocyanines (MIPCs), obtained upon interacting metalled phthalocyaninetetracarboxylic acid with 1-ethyl-3-methyl imidazolium chloride in a methanolic sodium hydroxide (NaOH) condition. Two MIPCs analyzed by 1H-NMR and MALDI-TOF, additionally, the four positional regioisomers (Cs, C4h, D2hand C2v) confirm by High Performance Liquid Chromatography (HPLC) analysis indicate the purity of the sample. The UV-visible and photoluminescence spectroscopy used to characterize the effects of peripheral substituents on the absorption and emission spectroscopy that featured the distinctive J(Jelly) and H(hypsochromic) aggregates of MIPCs in a polar solvent. Electrochemical characteristics evaluated through cyclic voltammetry (CV) confirms the redox properties and the electron transfer mechanism studied by DFT calculations. Gelation experiment demonstrated on zinc-ionic phthalocyanine shows the entangled network as evaluated using Scanning Electron Microscopy (SEM) images. We also studied the chromonic liquid crystalline behavior of MIPCs