Synthesis, physical properties and self-assembly of conjugated donor–acceptor system based on tetrathiafulvalene and functionalized with binding sites

A novel π-conjugated donor–acceptor compound (1) based on tetrathiafulvalene (TTF), which is functionalized with dipyridine, has been designed and synthesized. Spectroscopic and electrochemical behaviors of compound 1 demonstrate that the donor (TTF) unit strongly interacts with the electron-accepting group through the heteroaromatic bridge. The interaction of compound 1 with metallic ions can cause remarkable changes in the absorption and fluorescence spectra. DFT calculations reveal that the pyrazine ring is almost coplanar with the TTF plane, which is beneficial to the donor and acceptor electronic communication. Additionally, compound 1 can be self-assembled into nanostructures with smooth surface, hecto-nanometers in width and deca-micrometers in length.

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► Compound 1 has significantly intramolecular charge transfer interaction.
► Compound 1 with metallic ions can cause remarkable changes in the spectra.
► The pyrazine ring in compound 1 is almost coplanar with the TTF plane.
► Compound 1 has been self-assembled into micro/nanostructures.