Synthesis of non-peripheral thioanisole-substituted phthalocyanines: Photophysical, electrochemical, photovoltaic, and sensing properties

Abstract

Abstract This work reports on the synthesis, characterization, photophysical, electrochemical, photovoltaic and sensing properties of non-peripherally tetra 4-(methylthio)phenoxy substituted metal-free (2), Zn(II) (3) and Co(II) (4) phthalocyanine derivatives. Confirmation of the synthesized phthalocyanine structures which have the good solubility in organic solvents, performed with a combination of elemental analysis, FTIR, 1H NMR, 13C NMR, UV–vis and MALDI-MS spectral data. Electrochemical measurements exhibit that the complex (4) shows the redox reactions taking place on both metal center and the ring while the phthalocyanines (2) and (3) give only ring-based redox reactions. All the complexes were examined for utilization in dye-sensitized solar cells (DSSCs) in the presence of chenodeoxycholic acid and the highest power conversion efficiency was achieved for the complex (3), as 1.09%. The interaction of phthalocyanines (2) and (3) with Ag+ and Pd2+ ions and their aggregation properties (H- or J- Aggregation) were investigated by UV–vis spectroscopy. Photophysical (fluorescence quantum yield) properties of the complexes (2) and (3) were reported in different solvents, such as tetrahydrofuran (THF) and dimethyl sulfoxide (DMSO). The results of spectral measurements in these solvents showed that ΦF value of the complexes (2) and (3) were found to be lower than the unsubstituted ZnPc.