869796-30-5Relevant academic research and scientific papers
Tetrathiafulvalene-hydroxyamides and -oxazolines: Hydrogen bonding, chirality, and a radical cation salt
Réthoré, Céline,Fourmigué, Marc,Avarvari, Narcis
, p. 10935 - 10942 (2005)
Racemic and enantiopure ethylenedithio-tetrathiafulvalene (EDT-TTF) derivatives featuring β-hydroxyamide or oxazoline (OX) groups bearing methyl or isopropyl substituents have been synthesized starting from the corresponding amino alcohols. Crystal structure analysis shows in the case of the racemic methyl-β-hydroxyamide donor the development of a unique hydrogen bond network, characterized by short CO?H-O and N-H?O-H intermolecular distances. The enantiopure (S)-EDT-TTF-methyl-OX crystallizes in the monoclinic non-centrosymmetric space group P21, whereas the isopropyl counterparts, (R)-and (S)-EDT-TTF-isopropyl-OX, crystallize in the orthorhombic non-centrosymmetric space group P21212 1. All of them adopt a s-trans conformation in which TTF and oxazoline units are coplanar. Electrocrystallization experiments with the racemic EDT-TTF-methyl-OX, in the presence of (nBu4) 2Mo6Cl14 as supporting electrolyte, afford a radical cation salt, formulated as [(±)-EDT-TTF-methyl-OX] 2Mo6Cl14, in which the donors associate in strong dimers, which further stack along the b direction to form quasi-homochiral helix-like ribbons.
