The synthesis and electrochemical properties of a new tetra-(crown-ether-thiafulvalene)-annulated phthalocyanine derivative

A novel, metal-free, crown-ether-tetrathiafulvalene annulated phthalocyanine was synthesized by tetramerization of the corresponding phthalonitrile derivative; both compounds were characterized by elemental analysis, IR, UV–vis, DPV or CV and MS spectra. The crystal structure of the precursor was determined by X-ray crystallography. The charge transfer absorption bands of the two compounds lay ∼400 nm after addition of 7,7,8,8-tetracyanoquinodimethane. Electrochemical studies revealed that both compounds displayed good complexation selectivity for Na+ ion with large positive redox shifts, indicating that they may be a new redox-active sensor.