Synthesis and investigation of spectral and electrochemical properties of alkyl-substituted planar binuclear phthalocyanine complexes sharing a common naphthalene ring

Hexa-tert-butyl and dodeca-n-butyl-substituted planar binuclear phthalocyanines sharing a common naphthalene ring with Mg as a central metal were synthesized with high yields and characterized by UV/Vis spectra, luminescence spectra, NMR, electrochemical, and spectroelectrochemical measurements. On the base of these complexes, the metal-free phthalocyanine ligands and the series of binuclear phthalocyanine complexes of rare earth elements (REE) were synthesized.All compounds obtained revealed an intensive near IR-absorption reaching 855 nm for trinuclear phthalocyanine. A crucial increase in NMR spectra resolution was achieved by the addition of ethylene glycol as a disaggregating agent. Spectroelectrochemical measurements during oxidation showed reversible changes of absorbance at 709 and 800 nm.

Graphical abstractAlkyl-substituted planar binuclear phthalocyanines sharing a common naphthalene ring were synthesized and characterized by UV/Vis spectra, NMR, and electrochemical measurements. In order to interpret absorption bands in UV/Vis spectra, the fluorescence spectra were investigated. The influence of solvent nature and temperature on the character of 1H NMR spectra was considered.Figure optionsDownload full-size imageDownload as PowerPoint slide