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A novel magnesium-base and metal-free norphthalocyanine ( 6 and 7 ) containing peripheral thiacrown ether-linked tetrathiafulvalene moieties have been synthesized and fully characterized. Electrochemical investigations showed two quasi-reversible one-electron oxidation waves, one irreversible one-electron oxidation wave and two irreversible one-electron reduction waves, indicating that these triads are good π-electron donors. Triad 6 reacted with 2,3,5,6-tetrafluoro-7,7,8,8-tetra-cyanoquinodimethane (F 4 TCNQ) to form a charge transfer complex that exhibited absorption bands in the vicinity of 750 and 960 nm. Compound 6 showed evident intramolecular charge transfer interactions in ground states and these may be explained on the basis of the density functional theory. [ABSTRACT FROM AUTHOR]

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 (F 4 TCNQ). 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. Image 1 • 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. [ABSTRACT FROM AUTHOR]