Highly conjugated donor-acceptor dyad based on monotetrathiafulvalene covalently attached to a magnesium norphthalocyanine unit

A novel highly conjugated donor–acceptor dyad composed of a tetrathiafulvalene (TTF) moiety covalently attached to a magnesium norphthalocyanine (NPc) unit (1) has been synthesized and full characterized. Ultraviolet–visible spectroscopy and electron paramagnetic resonance data reveal that 1 forms an electron transfer complex with 2,3,5,6-tetrafluoro-7,7,8,8-tetra-cyanoquinodimethane (F4TCNQ). Detailed electrochemical investigations show one irreversible one-electron oxidation wave, two quasi-reversible one-electron oxidation waves, and two irreversible one-electron reduction waves, indicating that 1 is a good π-electron donor. Compound 1 shows clear intramolecular charge transfer (ICT) interactions from the tetrathiafulvalene fragments to the norphthalocyanine core. This phenomenon can be explained by density functional theory (DFT). A novel highly conjugated donor–acceptor dyad with tetrathiafulvalene (TTF) covalently attached to a magnesium norphthalocyanine (NPc) unit was synthesized. [Display omitted] •A novel highly conjugated donor–acceptor dyad was synthesized.•The electrochemical and optical properties of 1 are fully studied.•The results demonstrate that 1 is a good π-electron donor which has clear intramolecular charge transfer (ICT) interactions in molecule.