Molecular tectonics: enantiomerically pure chiral crystals based on trans -1,2-cyclohexanediol

Benjamin Forquin , Julien Berthaud , Abdelaziz Jouaiti (1) , Nathalie Kyritskas , Sylvie Ferlay , Mir Wais Hosseini

1 CMC - Chimie de la matière complexe

Enantiomerically pure chiral trans-1,2-cyclohexanediol ((R,R) or (S,S)) based organic compounds 3b-c bearing two benzoic acid moieties are self complementary units and thus self-assemble in the crystalline phase into isostructural crystals composed of 1D helical H-bonded networks with opposite handedness. The helical strands form enantiomerically pure triple helices. The racemic mixture of the two chiral ligands 3a also self-assembles into a 1D achiral H-bonded networks displaying a zigzag type geometry. Upon deprotonation, both chiral 3b and 3c bearing two carboxylate moieties behave as coordinating ligands. When combined with Cd(NO3)2 in the presence of ancillary N donor ligands such as Dabco (1,4-Diazabicyclo[2.2.2]octane) or bipy (4,4'bipyridine)), they lead to the formation of enantiomarically pure coordination networks. Whereas for both Cd-3b-Dabco and Cd-3c-Dabco) 1D networks, resulting from the interconnection of 2-2 metallamacrocycles by Dabco behaving as a linear connector, are observed, in the case of 4,4'Bipy connector (Cd-3b-Bipy and Cd-3c-Bipy) a 2D coordination network based on the interconnection of binuclear Cd(II) dimers by coordinating ligands and ancilary ligands is generated.

Domaines: Chimie

Benjamin Forquin, Julien Berthaud, Abdelaziz Jouaiti, Nathalie Kyritskas, Sylvie Ferlay, et al.. Molecular tectonics: enantiomerically pure chiral crystals based on trans -1,2-cyclohexanediol. CrystEngComm, 2019, 21 (34), pp.5129-5136. ⟨10.1039/c9ce00807a⟩. ⟨hal-03015875⟩