Ethylenedithio--Tetrathiafulvalene--Helicenes: Electroactive Helical Precursors with Switchable Chiroptical Properties

International audienceElectroactive fused ethylenedithio-tetrathiafulvalene-[4]helicene and -[6]helicenes have been synthesized through a strategy involving the preparation of 2,3-dibromo-helicene derivatives as intermediates. The dihedral angles between the terminal helicenes, as determined by single crystal X-ray analyses, amount to 22.7° and 50.7° for the [4]helicene and [6]helicene, respectively. The solid state architectures show interplay between S···S and ··· intermolecular interactions. The chiroptical properties of the enantiopure EDT-TTF-[6]helicene derivatives have been investigated and supported by TD DFT calculations. Remarkable redox switching of the circular dichroism signal between the neutral and radical cation species has been achieved