Helical organization of chiral binaphthyl tetrathiafulvaleneprimary amides through hydrogen bonding interactions

Abstract

Chiral tetrathiafulvalenes, (R) or (S), or racemic, (R,S), are obtained from a phosphite-mediated cross coupling reaction of a 1,3-dithiole-2-thione derivative bearing one binaphthol moiety, and are transformed into binaphthol-based tetrathiafulvalene ortho-diamides. The X-ray crystal structures of five intermediate chiral 1,3-dithiole-2-one and 1,3-dithiole-2-thione derivatives reveal the formation of helical structures through π–π interactions. The binaphthol-based tetrathiafulvalene ortho-diamides, as THF or DMSO solvates, adopt different solid-state organisations, characterised either by short intramolecular hydrogen bonds or with solely intermolecular hydrogen bonds and chiral solid-state structures with short intermolecular S⋯S contacts.