Synthesis, Characterization, Electrochemistry, and Spectroscopic Properties of Some Anthracenyl Functionalized Phthalocyanine Complexes of Ruthenium(II)

Abstract

The synthesis of single- and double-decked anthracenyl functionalized ruthenium(II) phthalocyanine complexes has been achieved through a controlled electrophilic aromatic substitution reaction of the free unsubstituted ruthenium(II) phthalocyanine with preformed 9-bromo-10-(2,3-dimethylacrylic acid)-anthracene and/or 9-bromo-10-(2,3-dimethylacrylic acid)-dianthracene using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as catalyst. The complexes were characterized by IR, UV-Vis, fluorescence, 1H, 13C NMR, and elemental analyses. A dimeric complex (C3R′′RuPc, where R′′ is 9-dianthracenyl-10-(2,3-dimethylacrylic acid), obtained as the major product of the dianthracenyl-substituted ruthenium phthalocyanine complex displays a strong near-infrared visible absorption band wavelength maxima at 1027 nm (ε=5.47×103 M−1 cm−1), with an interesting photoluminescent and electroredox active properties.