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Chiral bis(TTF) diamides have been obtained in good yields (54–74%) from 1,2-cyclohexane-diamine and the corresponding TTF acyl chlorides. The (<i>R</i>,<i>R</i>)-<b>1</b> and (<i>S</i>,<i>S</i>)-<b>1</b> enantiomers have been characterized by circular dichroism and the racemic form by single-crystal X-ray diffraction. The neutral racemic bis(TTF)-diamide shows the formation of a pincer-like framework in the solid state, thanks to the intramolecular S<b>···</b>S interactions. The chemical oxidation in a solution using FeCl₃ provides stable oxidized species, while the electrocrystallization experiments provided radical cation salts. In particular, single-crystal resistivity measurements on the racemic donor with AsF₆⁻ as a counterion demonstrate semiconductor behavior in this material. The DFT and TD-DFT calculations support the structural and chiroptical features of these new chiral TTF donors.