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Chiral Bis(tetrathiafulvalene)-1,2-cyclohexane-diamides.

ABSTRACT: Chiral bis(TTF) diamides have been obtained in good yields (54-74%) from 1,2-cyclohexane-diamine and the corresponding TTF acyl chlorides. The (R,R)-1 and (S,S)-1 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···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.

SUBMITTER: Bogdan A

PROVIDER: S-EPMC9611696 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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Chiral Bis(tetrathiafulvalene)-1,2-cyclohexane-diamides.

Bogdan Alexandra A Moraru Ionuț-Tudor IT Auban-Senzier Pascale P Grosu Ion I Pop Flavia F Avarvari Narcis N

Molecules (Basel, Switzerland) 20221015 20

Chiral bis(TTF) diamides have been obtained in good yields (54-74%) from 1,2-cyclohexane-diamine and the corresponding TTF acyl chlorides. The (R,R)-1 and (S,S)-1 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···S interactions. The chemical oxidat ...[more]

PMID: 36296517

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