Synthesis, electrochemical, and photophysical studies of hexadecachlorinatedphthalocyaninato zinc(II)

Synthesis of a new symmetrical 1,4,8,11,15,18,22,25-octahexyloxy-2,3,9,10,16,17,23,24-octa-(3,5-dichlorophenyl)phthalocyaninato zinc(II), ZnPc, has been described and characterized by 1H NMR, 13C NMR, MS, UV–Vis, and IR spectrometry. The newly prepared ZnPc is soluble in organic solvents and is not aggregated in solution. The photophysical properties were studied by steady-state absorption and emission, cyclic voltammetry, and nanosecond transient absorption techniques. The prepared ZnPc absorbs and emits at longer wavelengths compared to that of reported phthalocyanine derivatives. The electron-donating properties of the ZnPc have been examined by mixing it with the electron-accepting dicyanoperylene-3,4,9,10-bis(dicarboximide), PDICN2. The recorded nanosecond transient spectra in the visible/near-IR region showed clearly the electron-transfer from the triplet-excited state of the ZnPc to PDICN2 with a rate of 3.40 × 108 M−1 s−1. Light absorption in a wide section of the solar spectrum, favorable redox properties, and the electron-transfer properties suggest usefulness of the ZnPc in light-energy harvesting and developing optoelectronic devices.

► In this study we report the synthesis and characterization of a new symmetrical zinc phthalocyanine complex.
► We examine the photophysical and photochemical properties by the steady-state absorption and emission, cyclic voltammetry, and nanosecond transient absorption techniques.
► An efficient electron-transfer process from zinc phthalocyanine to perylenediimide has been reported in this study.